(3,5-Dimethoxyphenyl)acetic acid → N-[3-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-2-yl]-2-(3,5-dimethoxyphenyl)acetamide

HRID 1912912Notes

Reaction equation

HRID 1912912 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([OH:14])=O)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:23]([NH2:31])=[N:24][N:25]3[CH:30]=[CH:29][CH:28]=[N:27][C:26]=23)=[CH:18][CH:17]=1>>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:23]([NH:31][C:12](=[O:14])[CH2:11][C:5]3[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)=[N:24][N:25]3[CH:30]=[CH:29][CH:28]=[N:27][C:26]=23)=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 138316(3,5-Dimethoxyphenyl)acetic acidHCID 687512953-(4-Chlorophenyl)pyrazolo[1,5-a]pyrimidin-2-amine

Product 1

HCID 68748701N-[3-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-2-yl]-2-(3,5-dimethoxyphenyl)acetamideYield 8%

Procedure

3,5-Dimethoxyphenylacetic acid and the product from Example 99A were processed using the method analogous to that described in example 98 to afford 9 mg (8%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.36-10.57 (bs, 1H), 9.10 (dd, J=6.9, 1.7 Hz, 1H), 8.62 (dd, J=4.1, 1.7 Hz, 1H), 7.66-7.70 (m, 2H), 7.29-7.32 (m, 2H), 7.14 (dd, J=6.9, 4.1 Hz, 1H), 6.47-6.56 (bs, 2H), 6.44 (s, 1H), 3.73 (s, 6H), 3.58 (s, 2H); MS (ESI) m/z 423 (M+H)+.

Sources & evidence

ORD record
ord-0d0af6b18fb84e40b5d62145880db3c6
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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