3-Fluoroaniline → HCID 57737160, compound

HRID 1157573Notes

Reaction equation

HRID 1157573 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:18]3[CH:19]=[C:20]([NH:24][C:25](=[O:32])[CH2:26][C:27]4[S:28][CH:29]=[CH:30][CH:31]=4)[CH:21]=[CH:22][CH:23]=3)=[N:10][N:11]3[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.[F:33][C:34]1[CH:35]=[C:36]([CH:38]=[CH:39][CH:40]=1)[NH2:37]>>[F:17][C:15]1[CH:14]=[CH:13][C:12]2[N:11]([N:10]=[C:9]([C:18]3[CH:19]=[C:20]([NH:24][C:25](=[O:32])[CH2:26][C:27]4[S:28][CH:29]=[CH:30][CH:31]=4)[CH:21]=[CH:22][CH:23]=3)[C:8]=2[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:37][C:36]3[CH:38]=[CH:39][CH:40]=[C:34]([F:33])[CH:35]=3)[N:7]=2)[CH:16]=1

Participants

3

Reactant 2

HCID 97423-FluoroanilineHCID 57737205HCID 57737205, compound

Product 1

HCID 57737160HCID 57737160, compound

Procedure

The title compound was synthesized from N-{3-[3-(2-chloro-4-pyrimidinyl)-6-fluoropyrazolo[1,5-a]pyridin-2-yl]phenyl}-2-(2-thienyl)acetamide (0.070 g) and 3-fluoroaniline (0.033 g) using the procedure described in Example 30, step E. The title compound was isolated as a white solid (0.048 g, 66% yield). 1H NMR (400 MHz, DMSO-d6) δ 3.84 (s, 2H), 6.54 (d, 1H, J=5.52 Hz), 6.70 (m, 1H), 6.94 (m, 2H), 7.24 (m, 2H), 7.34-7.45 (m, 3H), 7.60 (m, 1H), 7.68-7.77 (m, 2H), 7.87 (s, 1H), 8.29 (d, 1H, J=5.52 Hz), 8.51 (m, 1H), 9.16 (m, 1H), 9.81 (s, 1H), 10.32 (s, 1H). ES-LC/MS m/z=539 [M+H]+.

Sources & evidence

ORD record
ord-dac74dcc580141d78d0500459a290fb1
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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