p-Fluorophenethylamine → HCID 11706135, compound

HRID 2074140Notes

Reaction equation

HRID 2074140 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1.C([O:13][C:14]([C:16]1[S:17][C:18]([N:21]2[CH2:26][CH2:25][N:24]([C:27](=[O:38])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]([F:37])([F:36])[F:35])[CH2:23][CH2:22]2)=[N:19][N:20]=1)=O)C>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:14]([C:16]2[S:17][C:18]([N:21]3[CH2:22][CH2:23][N:24]([C:27](=[O:38])[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:34]([F:37])([F:36])[F:35])[CH2:25][CH2:26]3)=[N:19][N:20]=2)=[O:13])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 4653p-FluorophenethylamineHCID 115823885-[4-(2-Trifluoromethylbenzoyl)piperazin-1-YL]-[1,3,4]thiadiazole-2-carboxylic acid ethyl ester

Product 1

HCID 11706135HCID 11706135, compound

Procedure

Following the procedure as described in Example 3, making variations only as required to use 2-(4-fluorophenyl)ethylamine in place of isoamylamine to react with 5[4-(2-trifluoromethylbenzoyl)piperazin-1-yl][1,3,4]thiadiazole-2-carboxylic acid ethyl ester, the title compound was obtained as a white solid (0.098 g, yield 98%). 1H NMR (300 MHz, CDCl3) δ 7.74-7.71 (m, 1H), 7.64-7.52 (m, 2H), 7.34-7.32 (m, 1H), 7.17-7.05 (m, 3H), 6.99-6.94 (m, 2H), 4.09-4.02 (m, 1H), 3.9-3.82 (m, 1H), 3.76-3.61 (m, 4H), 3.54-3.51 (m, 2H), 3.35-3.31 (m, 2H), 2.86 (t, J=7.2 Hz, 2H). 13C NMR (75 MHz, CDCl3) δ 174.5, 167.6, 163.3, 160.0, 158.3, 155.6, 134.1, 133.9, 132.4, 130.2, 130.1, 129.7, 129.1, 126.9, 126.7, 126.8, 125.4, 121.8, 115.6, 115.3, 49.5, 48.9, 45.9, 40.9, 40.7, 34.9. MS (ES+) m/z 508 (M+1).

Sources & evidence

ORD record
ord-19692a00f7d84595a1817f65c3d37522
Source dataset
uspto-grants-2011_04
Patent number
US07919496B2

Reaction notes

Loading…