Methylamine → HCID 59278217, compound

HRID 1698180Notes

Reaction equation

Br[C:2]1[S:3][C:4]([CH2:7][NH:8][C:9]([C:11]2[C:12]3[CH:19]=[N:18][N:17]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)[C:13]=3[CH:14]=[N:15][CH:16]=2)=[O:10])=[CH:5][N:6]=1.[CH3:27][NH2:28].C1COCC1.C([O-])([O-])=O.[K+].[K+]>[Cl-].[NH4+].CCOC(C)=O>[CH3:27][NH:28][C:2]1[S:3][C:4]([CH2:7][NH:8][C:9]([C:11]2[C:12]3[CH:19]=[N:18][N:17]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)[C:13]=3[CH:14]=[N:15][CH:16]=2)=[O:10])=[CH:5][N:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

1-(4-Fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid (2-bromo-thiazol-5-ylmethyl)-amide (50 mg, 0.10 mmol) was treated with a 2 M solution of methylamine in THF (2.0 mL, 4.0 mmol) in a microwave tube. To this solution was added solid K2CO3 (19 mg, 0.14 mmol), and the microwave tube was sealed and heated at 100° C. for 1 hour in a microwave. The mixture was then heated at 160° C. in a microwave for 4 hours, and the mixture was diluted with saturated aqueous ammonium chloride (40 mL) and EtOAc (20 mL). The layers were separated and the organics layer was washed with brine (50 mL), dried over sodium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography eluting with a gradient of 0-10% methanol in dichloromethane to afford the title compound.

Workup

customthe microwave tube was sealed
temperatureThe mixture was then heated at 160° C. in a microwave for 4 hours
customThe layers were separated
washthe organics layer was washed with brine (50 mL)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe crude material was purified by silica gel chromatography
washeluting with a gradient of 0-10% methanol in dichloromethane

Sources & evidence

ORD record: ord-51a7dcbc7b864adb8fc0c74eddc4c42d
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163918B2

Reaction notes

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