2,6-Difluorobenzoyl chloride → HCID 59511435, compound

HRID 1157613Notes

Reaction equation

HRID 1157613 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]([C:17]3[C:22]([F:23])=[CH:21][N:20]=[C:19]([NH:24][C:25]4[CH:34]=[C:33]5[C:28]([CH2:29][CH2:30][N:31]([CH3:35])[CH2:32]5)=[CH:27][CH:26]=4)[N:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[F:36][C:37]1[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[C:38]=1[C:39](Cl)=[O:40]>C1COCC1.CO>[F:36][C:37]1[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[C:38]=1[C:39]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[C:16]([C:17]3[C:22]([F:23])=[CH:21][N:20]=[C:19]([NH:24][C:25]4[CH:34]=[C:33]5[C:28]([CH2:29][CH2:30][N:31]([CH3:35])[CH2:32]5)=[CH:27][CH:26]=4)[N:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)[CH:3]=1)=[O:40]

Participants

5

Reactant 2

HCID 874382,6-Difluorobenzoyl chlorideHCID 11496393HCID 11496393, compound

Product 1

HCID 59511435HCID 59511435, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-{4-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-5-fluoro-2-pyrimidinyl}-2-methyl-1,2,3,4-tetrahydro-7-isoquinolinamine (50 mg, 0.11 mmol) in THF (5 mL) was added 2,6-difluorobenzoyl chloride (20 mg, 0.11 mmol) and the reaction mixture stirred at rt for 20 min. The reaction was diluted with MeOH, adsorbed onto silica gel, and purified by column chromatography (0-10% MeOH/DCM+1% NH4OH) to afford the title compound (15.4 mg, 24%) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 10.86 (s, 1H), 9.52 (s, 1H), 8.86 (d, J=7.69 Hz, 1H), 8.45-8.46 (m, 1H), 8.06 (s, 1H), 7.89 (d, J=8.61 Hz, 1H), 7.71-7.73 (m, 1H), 7.54-7.58 (m, 1H), 7.30-7.47 (m, 4H), 7.20-7.24 (m, 3H), 7.08-7.12 (m, 1H), 6.86 (d, J=8.42 Hz, 1H), 3.26 (s, 2H), 2.66-2.69 (m, 2H), 2.49-2.51 (m, 2H), 2.26 (s, 3H). ES-LC/MS m/z=606 [M+H]+.

Workup

  1. custompurified by column chromatography (0-10% MeOH/DCM+1% NH4OH)

Sources & evidence

ORD record
ord-dd4dc0c50eca48629cde9c6207ae1f95
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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