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

HRID 1912903Notes

Reaction equation

HRID 1912903 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C:9]([OH:11])=O)[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:4]3[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=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 27237243-Pyridineacetic acid, hydrochloride (1:1)HCID 687512953-(4-Chlorophenyl)pyrazolo[1,5-a]pyrimidin-2-amine

Product 1

HCID 68750818N-[3-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-2-yl]-2-(pyridin-3-yl)acetamide

Procedure

3-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 8.85 (dd, J=7.0, 1.8 Hz, 1H), 8.55 (dd, J=4.1, 1.8 Hz, 1H), 8.52-8.55 (m, 1H), 8.46-8.50 (m, 1H), 7.78-7.89 (m, 1H), 7.60-7.64 (m, 2H), 7.37-7.45 (m, 1H), 7.29-7.32 (m, 2H), 7.06 (dd, J=7.0, 4.1 Hz, 1H), 3.81 (s, 2H); MS (ESI) m/z 364 (M+H)+; Anal. calculated for C19H14ClN5O.0.35H2O: C, 61.66; H, 4.00; N, 18.92. Found C, 61.40; H, 3.70; N, 18.77.

Sources & evidence

ORD record
ord-3b11880501f34b04812d63f892e6d475
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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