2-Thiopheneacetyl chloride → N-{5-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]-2-fluorophenyl}-2-(2-thienyl)acetamide

HRID 1157637Notes

Reaction equation

HRID 1157637 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:17]3[CH:18]=[CH:19][C:20]([F:24])=[C:21]([CH:23]=3)[NH2:22])=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.[CH:25]1[CH:29]=[C:28]([CH2:30][C:31](Cl)=[O:32])[S:27][CH:26]=1>>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:17]3[CH:18]=[CH:19][C:20]([F:24])=[C:21]([NH:22][C:31](=[O:32])[CH2:30][C:28]4[S:27][CH:26]=[CH:25][CH:29]=4)[CH:23]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 1623622-Thiopheneacetyl chlorideHCID 577371725-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]-2-fluoroaniline

Product 1

HCID 57737159N-{5-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]-2-fluorophenyl}-2-(2-thienyl)acetamideYield 92.5%

Procedure

5-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]-2-fluoroaniline (690 mg, 2.0 mmol) and thiophene-2-acetyl chloride (0.26 mL, 2.1 mmol) were coupled according to the procedure of Example 56, Step G to give the desired product (858 mg, 92%). 1H NMR (400 MHz, d6-DMSO) δ 10.21 (s, 1H), 8.93 (d, J=9.2 Hz, 1H), 8.49 (d, J=7.6 Hz, 1H), 8.44 (d, J=12.0 Hz, 1H), 8.29-8.27 (m, 1H), 7.70-7.65 (m, 1H), 7.49-7.41 (m, 3H), 7.27-7.22 (m, 1H), 7.13 (d, J=7.2 Hz, 1H), 7.02-6.98 (m, 2H), 4.02 (s, 2H) ppm.

Sources & evidence

ORD record
ord-048d8989f4fd495a9efa123f04d24426
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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