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

HRID 1912902Notes

Reaction equation

HRID 1912902 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.[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:3]3[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=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 853172-Pyridineacetic acid, hydrochloride (1:1)HCID 687512953-(4-Chlorophenyl)pyrazolo[1,5-a]pyrimidin-2-amine

Product 1

HCID 68752365N-[3-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-2-yl]-2-(pyridin-2-yl)acetamideYield 45.1%

Procedure

2-Pyridylacetic acid hydrochloride (44 mg, 0.25 mmol) and the product from Example 99A (62 mg, 0.25 mmol) were processed as described in Example 98 to afford 41 mg (45%) of the title compound. 1H NMR (400 MHz, CD3OD) δ ppm 8.85 (dd, J=7.0, 1.7 Hz, 1H), 8.55 (dd, J=4.1, 1.7 Hz, 1H), 8.47-8.53 (m, 1H), 7.77-7.86 (m, 1H), 7.68-7.71 (m, 2H), 7.40-7.48 (m, 1H), 7.31-7.40 (m, 3H), 7.05 (dd, J=7.0, 4.1 Hz, 1H), 3.97 (s, 2H); MS (ESI) m/z 364 (M+H)+; Anal. calculated for C19H14ClN5O: C, 62.73; H, 3.88; N, 19.25. Found C, 62.65; H, 3.65; N, 19.19.

Sources & evidence

ORD record
ord-d5bd6865c9a24d5f87aa64f71080149a
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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