Trifluoroacetic acid → 3-Amino-6-cyclopropyl-pyridine-2-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

HRID 2219585Notes

Reaction equation

HRID 2219585 reaction equation
C(OC(=O)[NH:7][C:8]1[C:9]([C:17](=[O:25])[NH:18][C:19]2[CH:23]=[CH:22][N:21]([CH3:24])[N:20]=2)=[N:10][C:11]([CH:14]2[CH2:16][CH2:15]2)=[CH:12][CH:13]=1)(C)(C)C.FC(F)(F)C(O)=O.C(OCC)(=O)C.C(=O)(O)[O-].[Na+].O>C(Cl)Cl>[CH3:24][N:21]1[CH:22]=[CH:23][C:19]([NH:18][C:17]([C:9]2[C:8]([NH2:7])=[CH:13][CH:12]=[C:11]([CH:14]3[CH2:16][CH2:15]3)[N:10]=2)=[O:25])=[N:20]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 23687555EtOAc water NaHCO3HCID 69233332[6-Cyclopropyl-2-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-pyridin-3-yl]-carbamic acid tert-butyl ester

Product 1

HCID 866075993-Amino-6-cyclopropyl-pyridine-2-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amideYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 70 mg (0.228 mmol) of [6-Cyclopropyl-2-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-pyridin-3-yl]-carbamic acid tert-butyl ester in 3 ml of methylene chloride was treated with 0.26 ml (0.39 g, 3.42 mmol, 15 equiv.) of trifluoroacetic acid. After stirring for 2.5 h at room temperature, the mixture was worked up with Ethyl acetate/Sodium bicarbonate/water to yield 49 mg (0.19 mmol, 83%) of crude title compound as a light yellow solid, MS (ISP): m/e=258.1 (M+H+); which was sufficiently pure to be used directly in the next step.

Sources & evidence

ORD record
ord-cfe7f42e789f4f59ac54276e955404b8
Source dataset
uspto-grants-2008_08
Patent number
US07414060B2

Reaction notes

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