Propionic Acid → 2-(5-isoquinolinyl)-N-{4-[(trifluoromethyl)thio]benzyl}propanamide

HRID 2056914Notes

Reaction equation

[F:1][C:2]([F:13])([F:12])[S:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=1.[C:14]([OH:18])(=O)[CH2:15][CH3:16].[CH:19]1[C:28]2[C:23](=[C:24](CC(O)=O)[CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][N:20]=1>>[CH:19]1[C:28]2[C:23](=[C:24]([CH:15]([CH3:16])[C:14]([NH:9][CH2:8][C:7]3[CH:10]=[CH:11][C:4]([S:3][C:2]([F:12])([F:1])[F:13])=[CH:5][CH:6]=3)=[O:18])[CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][N:20]=1

Participants

Reactant 3

HCID 1032Propionic Acid

HCID 27778754-(Trifluoromethylthio)benzylamine

HCID 120187082-(Isoquinolin-5-YL)acetic acid

Product 1

HCID 100232722-(5-isoquinolinyl)-N-{4-[(trifluoromethyl)thio]benzyl}propanamide

Procedure

The title compound was prepared using the procedure described in Example 222B using 4-[(trifluoromethyl)thio]benzylamine and 2-5-isoquinolinyl)propanoic acid instead of 4-(trifluoromethoxy)benzylamine and 5-isoquinolinylacetic acid. MS (ESI+) m/z 391 (M+H)+; MS (ESI−) m/z 389 (M−H)−; 1H NMR (DMSO, 300 MHz) δ 1.57 (d, J 7.1, 3H), 4.33 (d, J 6.1, 2H), 4.65 (q, J 7.1, 1H), 7.33 (d, J 8.1, 1H), 7.65 (m, 2H), 7.76 (m, 1H), 7.98 (m, 2H), 8.19 (d, J 7.1, 1H), 8.42 (d, J 7.8, 1H), 8.61 (br s, 1H), 8.62 (d, J 6.8, 1H), 8.73 (d, J 6.8, 1H), 8.96 (t, J 5.8, 1H), 9.86 (s, 1H); Anal. Calcd for C20H17F3N2OS+2.1 HCl: C, 51.44; H, 4.12. Found: C, 51.35; H, 3.91.

Sources & evidence

ORD record: ord-96db9e37ca654a1db8b79fd24d9a0d8b
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07335678B2

Reaction notes

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