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Home > Encyclopedia > 2-HYDROXY-3-PYRAZINECARBOXYLIC ACID

2-HYDROXY-3-PYRAZINECARBOXYLIC ACID

2-HYDROXY-3-PYRAZINECARBOXYLIC ACID structure
  • CAS No:

    20737-42-2

  • Formula:

    C5H4N2O3

  • Synonyms:

    3-HYDROXY-PIPERAZINE-2-CARBOXYLIC ACID;3-HYDROXYPYRAZINE-2-CARBOXYLIC ACID;2-HYDROXY-3-PYRAZINECARBOXYLIC ACID;3-Hydroxy-2-pyrazinecarboxylic acid;3-hydroxy-2-pyrazinecarboxylic acid(SALTDATA: FREE);3-Hydroxypyrazinecarboxylic acid;3-Hydroxypyrazine-2-carbo...;2-Carboxy-3-hydroxypyrazine

  • Categories:

    Pharmaceutical Intermediates  >  Heterocyclic Compound

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Basic Attributes

  • 20737-42-2

  • C5H4N2O3

  • 140.1

  • 140.022186

  • 78.8

  • -0.2

  • FJZRUSFQHBBTCC-UHFFFAOYSA-N

  • 4

  • 2

  • 0.00

  • 1

Characteristics

  • 1.6±0.1 g/cm3

  • 218-220 °C

  • 305.2°C at 760 mmHg

  • 321.8±31.5 °C

  • 1.639

Safety Information

Production Methods

3-[3-(5-CHLORO-lH-BENZOIMIDAZOL-2-YL)-AZETIDIN-l-YL]- PYRAZI E-2-CARBOXYLIC ACID M ESTEP 1. 3 -HYDROXY-P YRAZINE-2 -C ARB OXYLIC ACID; [00201 ] The 3-amino-pyrazine-2-carboxylic acid (6.95 g, 0.05mmol) was dissolved in a mixture of water (55 mL) and sulfuric acid (55 mL, 3.75M) and heated to 50 °C. A solution of sodium nitrite (18.5 mL, 0.06 mmol) was added to the above solution which was cooled to 12 °C. The temperature was maintained at 10-16 °C over 30 mins during addition period and then the mixture was heated to boiling over a period of 30 mins. After cooling to RT, the yellow solid was collected by filtration. The solid was dissolved in a dilute sodium bicarbonate solution, the carboxylic acid product precipitated by treatment with hydrochloric acid (10percent) and collected by filtration, the crude carboxylic acid product was recrystallized from water to give a yellow- orange crystalline solid (4.1g, yield 58percent).Example 4 (6-Chloro-lH-indol- -yl)[2-[(4-fluorobenzyl)amino]pyrazin-3-yl]methanone 3-Hydroxy-2-pyrazinecarboxylic acid. A suspension of 3-amino-2- pyrazinecarboxylic acid (1.42 g, 10.2 mmol) in water (11.5 mL) was treated with a 3.75 M HPreparation of methyl (S)-3-(4-cyanophenyl)-2-((4-((3-((4-(3-hydroxypyrazine-2- carbonyl)piperazin-1-yl)methyl)phenyl)amino)-1, 3, 5-triazin-2-yl)amino)propanoate (TA1026). HATU (1.2 equiv., 45 mg, 0.12 mmol) was added to a solution of 3- hydroxypyrazine-2-carboxylic acid (I-6, 1.1equiv., 15 mg, 0.11 mmol) in anhydrous DCM (1.5 mL) and DIPEA (3equiv., 0.040 mL, 0.23 mmol). After being stirred at r.t.10 minutes, TA1047 (1equiv., 46 mg, 0.098 mmol) was added. The resulting suspension was stirred at r.t. 1 h, followed by DMF (0.1 mL). Then the reaction was stirred for another 2 h until the LCMS analysis showed complete consumption of the starting material. The crude residue was then purified by reverse phase preparative HPLC (XBridge BEH, 19x150 mm, 5mum, C18 column; ACN/water with 0.1% formic acid modifier, 20mL/min), affording Compound TA1026 (15.1 mg, 25%) as a yellow solid.1H NMR (400 MHz, Methanol-d4) d 8.12 (d, J = 10.2 Hz, 1H), 7.71 - 7.65 (m, 2H), 7.61 (d, J = 8.0 Hz, 2H), 7.49 (s, 2H), 7.43 (d, J = 7.9 Hz, 3H), 7.34- 7.27 (m, 1H), 7.08 (dd, J = 17.7, 7.0 Hz, 1H), 4.96 (dd, J = 8.6, 5.8 Hz, 1H), 3.83- 3.77 (m, 2H), 3.71 (s, 2H), 3.60 (s, 2H), 3.43- 3.39 (m, 3H), 3.25- 3.14 (m, 3H), 2.58 (dt, J = 36.9, 4.7 Hz, 5H). MS (m/z): 595 [M+1]+, LCMS purity: 99%.Preparation of methyl (S)-3-(4-cyanophenyl)-2-((4-(((5-fluoro-1H- benzo[d]imidazol-2-yl)methyl)amino)-6-((3-((4-(3-hydroxypyrazine-2-carbonyl)piperazin- 1-yl)methyl)phenyl)amino)-1, 3, 5-triazin-2-yl)amino)propanoate (TA1020). Prepared in an analogous manner to example 001, step 4. HATU (1.2 equiv., 36 mg, 0.094 mmol) was added to a solution of Preparation of (S)-3-(4-cyanophenyl)-2-((4-(((5-fluoro-1H-benzo[d]imidazol- 2-yl)methyl)amino)-6-((3-((4-(3-hydroxypyrazine-2-carbonyl)piperazin-1- yl)methyl)phenyl)amino)-1, 3, 5-triazin-2-yl)amino)-N, N-dimethylpropanamide (TA1021). HATU (1.2 equiv., 34 mg, 0.093 mmol) was added to a solution of 3-hydroxypyrazine-2- carboxylic acid (I-6, 1.1equiv., 12 mg, 0.080 mmol, Synthonix, Fisher Scientific) in anhydrous DCM (0.70 mL) and DIPEA (3equiv., 0.040 mL, 0.23 mmol). After being stirred at r.t. for 10 minutes, TA1013 (50 mg, 0.080 mmol) was added. The reaction was stirred at r.t. until the LCMS analysis showed complete consumption of the starting material (3-24h). The crude residue was then purified by reverse phase preparative HPLC (XBridge BEH, 19x150 mm, 5mum, C18 column; ACN/water with 0.1% formic acid modifier, 20mL/min), affording Compound TA1021 (17.3 mg, 29%) as an orange solid. 1H NMR (400 MHz, DMSO-d6) d 12.20 (s, 1H), 8.95 (d, J = 24.1 Hz, 1H), 8.07- 7.87 (m, 1H), 7.84- 7.68 (m, 1H), 7.68- 7.41 (m, 4H), 7.40- 7.22 (m, 2H), 7.22- 6.78 (m, 3H), 6.56 (s, 1H), 5.18- 4.91 (m, 1H), 4.79- 4.50 (m, 2H), 3.74- 3.39 (m, 7H), 3.28- 3.13 (m, 4H), 3.12- 2.78 (m, 5H), 2.75- 2.66 (m, 1H), 2.61 (s, 1H), 2.48- 2.02 (m, 4H). MS (m/z): 771 [M+1]+, LCMS purity: 99%.

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