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

HRID 1912942

Reaction equation

HRID 1912942 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.[F:15][C:16]1[CH:17]=[C:18]([C:22]2[C:23]([NH2:31])=[N:24][N:25]3[CH:30]=[CH:29][CH:28]=[N:27][C:26]=23)[CH:19]=[CH:20][CH:21]=1>>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([CH2:11][C:12]([NH:31][C:23]2[C:22]([C:18]3[CH:19]=[CH:20][CH:21]=[C:16]([F:15])[CH:17]=3)=[C:26]3[N:27]=[CH:28][CH:29]=[CH:30][N:25]3[N:24]=2)=[O:14])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

3

Reactant 2

HCID 138316(3,5-Dimethoxyphenyl)acetic acidHCID 68751731HCID 68751731, compound

Product 1

HCID 687489772-(3,5-dimethoxyphenyl)-N-[3-(3-fluorophenyl)pyrazolo[1,5-a]pyrimidin-2-yl]acetamide

Procedure

3,5-Dimethoxyphenylacetic acid and the product from Example 128A were processed as using the method analogous to that described in example 104 to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.40-10.51 (bs, 1H), 9.11 (dd, J=7.0, 1.8 Hz, 1H), 8.65 (dd, J=4.1, 1.7 Hz, 1H), 7.59 (ddd, J=11.2, 2.6, 1.6 Hz, 1H), 7.52 (d, J=7.9 Hz, 1H), 7.26-7.34 (m, 1H), 7.16 (dd, J=7.0, 4.1 Hz, 1H), 7.02-7.09 (m, 1H), 6.46-6.54 (m, 2H), 6.38-6.43 (m, 1H), 3.67-3.77 (bs, 6H), 3.59-3.62 (bs, 2H); MS (ESI) m/z 407 (M+H)+. Anal. calculated for C22H19FN4O3: C, 65.02; H, 4.71; N, 13.79. Found C, 64.80; H, 4.54; N, 13.77.

Sources & evidence

ORD record
ord-50475ca0ee864b4a8bfe11e70b89a70c
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Linked notes

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