5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid
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![5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid structure](https://file.echemi.com/fileManage/upload/canonicalSmiles/20220812/45606230c47148f0b3b09f54a64204cd.png "5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid")
5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid
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CAS No:
800401-68-7
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Formula:
C8H5ClN2O2
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Chemical Name:
5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid
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Synonyms:
1H-Pyrrolo[2,3-c]pyridine-2-carboxylic acid,5-chloro-;5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid
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CAS No:
5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid Basic Attributes
196.59
196.59
DTXSID80660000
2933990090
5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid Use and Manufacturing
General procedure: To a stirred solution of 9a–d (1.3 mmol) in EtOH (12 mL) 2M NaOH was added (1.7 mmol, 1.1 mL).The reaction mixture was heated under reflux for 1h (10a) or 2h (10b) and the solvent was evaporated.Water (10 mL) was added and acetic acid was added until pH 4.0. The desired product was filtered off, dried into the desiccators to afford the desired product.(2?>5-Chloro-lH-pyrrolo[2, 3-c]pyridine-2-carboxylic acid (2-oxo-l, 2, 3, 4- tetrahydroquinolin-3-yl)amide; To a suspension of 3-(3?^-amino-3, 4-dihydro-lH-quinolin-2-one hydrochloride (Preparation24, 67mg, 0.34mmol) in DMF (5mL) under argon was added DIPEA (186muL, 1.07mmol), 5-chloro- lH-pyrrolo[2, 3-c]pyridine-2-carboxylic acid (Preparation 3, 60mg, 0.31mmol) and EtaOBt (51mg, 0.34mmol) and the reaction stirred for 5min. EDCI (76mg, 0.5mmol) was added and the reaction stirred for 16h at rt. Solvent was removed in vacuo and the residue partitioned between EtOAc (5OmL) and water (4OmL). Organics were washed with NaHCO3 solution (2x15mL) then brine (15mL) before being dried (MgSO4) and solvent removed in vacuo. Purification by crystallisation from methanol afforded the title compound. deltaH(d6 DMSO): 8.61 (IH, s), 7.80 (IH, s), 129-1 Al (3H, m), 7.00-6.90 (2H, m), 4.82-4.73 (IH, m), 3.22-3.06 (2H, m); m/z (ES+) = 341.03 [M+ H]+; RT = 3.24min.
Computed Properties
Molecular Weight:196.59
XLogP3:1.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:196.0039551
Monoisotopic Mass:196.0039551
Topological Polar Surface Area:66
Heavy Atom Count:13
Complexity:224
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid
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