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3-(BOC-AMINO)PYRIDINE

3-(BOC-AMINO)PYRIDINE structure

CAS No:
56700-70-0
Formula:
C10H14N2O2
Chemical Name:
3-(BOC-AMINO)PYRIDINE
Synonyms:
TERT-BUTYL PYRIDIN-3-YLCARBAMATE;3-(BOC-AMINO)PYRIDINE;3-TERT-BUTOXYCARBONYLAMINOPYRIDINE;Carbamic acid, 3-pyridinyl-, 1,1-dimethylethyl ester (9CI);tert-butyl N-(pyridin-3-yl)carbaMate;3-(Boc-aMino)pyridine 97%;BOC-3-Amino pyridine
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

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3-(BOC-AMINO)PYRIDINE Basic Attributes

Molecular Weight：

194.23

Exact Mass：

194.105530

DSSTox ID：

DTXSID60448782

HScode：

2933399090

Characteristics

PSA：

51.2

XLogP3：

1.8

Density：

1.1±0.1 g/cm3

Melting Point：

116-120 °C(lit.)

Flash Point：

106.7±19.8 °C

Refractive Index：

1.544

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

22-43

safety instructions：

36/37

Marks：

Precautionary statement(s)：

P280

Hazard Statements：

H302-H317

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

3-(BOC-AMINO)PYRIDINE Use and Manufacturing

3-Aminopyridine (4.29 g, 45.. 6 mmol) was dissolved in THF (100 mL). A 1 M THF solution of sodium hexamethyl-disilazide (NaHMDS, 100 mL, 100 mmol) was added dropwise via an addition funnel. After 15 min, a solution of di-t-butyl dicarbonate[ (Boc) 201 (11.92 g, 54.6 mmol) in THF (100 mL) was added dropwise. After 15 min, the reaction was quenched with water (100 mL) and extracted with EtOAc (500 mL). The organic layer was washed with water (2 x 100 mL). The aqueous layers were combined and extracted with EtOAc (200 mL). The organic layers were combined, dried over sodium sulfate, filtered, and concentrated. The crude material was purified by flash column chromatography (30percentEtoAc/CH2C12) to give the desired product (5.195 g, 30.5 mmol, 67percent) as an orange solid. 1NMR (400 MHz, DMSO-d6) 9.53 (s, 1H) ; 8. 57 (s, 1H) ; 8. 14 (d, J=4.4 Hz, 1H) ; 7.84 (d, J=8.0 Hz, 1H) ; 7.25 (m, 1H) ; 1.44 (s, 9H). To a solution of pyridin-3 -amine (2.5 g, 26.3 mmol) in anhydrous tetrahydiOfuran (80 mL) was added 1 M sodium bis(trimethylsilyl)amide in tetrahydrofuran (52.6 mL, 52.6 mmol) in a steady stream. The mixture was stirred for 30 minutes, treated dropwise with a solution of di-feri-butyl dicarbonate (5.92 g, 26.3 mmol) in anhydrous tetrahydrofuran (20 mL), stirred for 3 hours and concentrated. The residue was dissolved in ethyl acetate, washed with saturated aqueous sodium chloride, dried over anhydrous MgSCu, filtered, and concentrated by rotary evaporation. Purification by chromatography on silica eluting with 3percent> methanol in dichloromethane afforded an amber semisolid. The material was dissolved in ethyl acetate, treated with decolorizing charcoal and vacuum filtered through diatomaceous earth. Concentration of the filtrate by rotary evaporation afforded the title compound as a light gold solid (4.35 g, 85percent). MS (DCI+) m/z 195 (M+H)

Computed Properties

Molecular Weight:194.23
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:194.105527694
Monoisotopic Mass:194.105527694
Topological Polar Surface Area:51.2
Heavy Atom Count:14
Complexity:199
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes