4-Pyridineacetic acid hydrochloride → N-[3-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-2-yl]-2-(pyridin-4-yl)acetamide

HRID 1912904Notes

Reaction equation

HRID 1912904 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:20]([NH2:28])=[N:21][N:22]3[CH:27]=[CH:26][CH:25]=[N:24][C:23]=23)=[CH:15][CH:14]=1>>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:20]([NH:28][C:9](=[O:11])[CH2:8][C:5]3[CH:4]=[CH:3][N:2]=[CH:7][CH:6]=3)=[N:21][N:22]3[CH:27]=[CH:26][CH:25]=[N:24][C:23]=23)=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 810974-Pyridineacetic acid hydrochlorideHCID 687512953-(4-Chlorophenyl)pyrazolo[1,5-a]pyrimidin-2-amine

Product 1

HCID 68751697N-[3-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-2-yl]-2-(pyridin-4-yl)acetamide

Procedure

4-Pyridylacetic acid hydrochloride and the product from Example 99A were processed using method analogous to that described in Example 98 to afford the title compound. 1H NMR (400 MHz, CD3OD) δ ppm 8.86 (dd, J=7.1, 1.6 Hz, 1H), 8.56 (dd, J=4.1, 1.8 Hz, 1H), 8.45-8.53 (m, 2H), 7.57-7.66 (m, 2H), 7.37-7.48 (m, 2H), 7.26-7.35 (m, 2H), 7.07 (dd, J=7.0, 4.1 Hz, 1H), 3.82 (s, 2H); MS (ESI) m/z 364 (M+H)+; Anal. calculated for C19H14ClN5O.0.25H2O: C, 61.69; H, 3.97; N, 18.68. Found C, 61.59; H, 3.61; N, 18.68.

Sources & evidence

ORD record
ord-440a5cb022184ecb8ecd0eb92719cf7d
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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