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

HRID 1157641Notes

Reaction equation

HRID 1157641 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]([O:24][CH3:25])=[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:26]1[CH:30]=[C:29]([CH2:31][C:32](Cl)=[O:33])[S:28][CH:27]=1>>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:17]3[CH:18]=[CH:19][C:20]([O:24][CH3:25])=[C:21]([NH:22][C:32](=[O:33])[CH2:31][C:29]4[S:28][CH:27]=[CH:26][CH:30]=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 577371655-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]-2-(methyloxy)aniline

Product 1

HCID 57737232N-{5-[3-(2-chloropyrimidin-4-yl)pyrazolo[1,5-a]pyridin-2-yl]-2-methoxyphenyl}-2-(2-thienyl)acetamideYield 84%

Procedure

5-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]-2-(methyloxy)aniline (400 mg, 1.14 mmol) and thiophene-2-acetyl chloride (148 mL, 1.50 mmol) were coupled according to the procedure of Example 56, Step G to give the desired product (454 mg, 84%). 1H NMR (400 MHz, d6-DMSO) δ 9.51 (s, 1H), 8.87 (D, J=7.2 Hz, 1H), 8.42-8.38 (m, 2H), 8.27 (s, 1H), 7.61 (d, J=8.0 Hz, 1H), 7.37-7.36 (m, 1H), 7.30 (dd, J=8.4 and 2.0 Hz, 1H), 7.19-7.16 (m, 2H), 7.09 (d, J=5.6 Hz, 1H), 6.96-6.94 (m, 2H), 3.98 (s, 2H), 3.91 (s, 3H) ppm.

Sources & evidence

ORD record
ord-06d47e2554af4aa9a8752725b9157051
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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