4-Fluoroaniline → HCID 24951500, compound

HRID 1879204Notes

Reaction equation

HRID 1879204 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:17]2[CH:21]=[CH:20][N:19]([CH2:22][CH2:23]OS(C)(=O)=O)[N:18]=2)[S:5][C:6]=1[C:7](=[O:16])[NH:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.[F:29][C:30]1[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=1>>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH2:9][NH:8][C:7]([C:6]2[S:5][C:4]([C:17]3[CH:21]=[CH:20][N:19]([CH2:22][CH2:23][NH:36][C:33]4[CH:34]=[CH:35][C:30]([F:29])=[CH:31][CH:32]=4)[N:18]=3)=[N:3][C:2]=2[CH3:1])=[O:16])[CH:11]=1

Participants

3

Reactant 2

HCID 97314-FluoroanilineHCID 59489547HCID 59489547, compound

Product 1

HCID 24951500HCID 24951500, compound

Procedure

The title compound was prepared from methanesulfonic acid 2-(3-{4-methyl-5-[(pyridin-3-ylmethyl)-carbamoyl]-thiazol-2-yl}-pyrazol-1-yl)-ethyl ester and 4-fluoro-phenylamine as describe in Example 77 and isolated as a white solid (0.032 g, 53% yield). 1H NMR (400 MHz, CDCl3) δ 8.63 (s, 1H), 8.56 (d, J=4 Hz, 1H), 7.72 (d, J=8 Hz, 1H), 7.39 (d, J=2 Hz, 1H), 7.28-7.34 (m, 1H), 6.89 (t, J=8 Hz, 2H), 6.83 (d, J=2 Hz, 1H), 6.51-6.56 (m, 2H), 6.09 (bs, 1H), 4.65 (d, J=8 Hz, 2H), 4.47 (t, J=6 Hz, 2), 3.58-3.63 (m, 2H), 2.76 (s, 3H); MS (M+H)+=436.9; Rt=1.20 min; HRMS (M+H)+=437.12.

Sources & evidence

ORD record
ord-18814fcaf8354c45b29645726c93992b
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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