Hexylamine → HCID 11612494, compound

HRID 2074132Notes

Reaction equation

HRID 2074132 reaction equation
[CH2:1]([NH2:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C([O:10][C:11]([C:13]1[S:14][C:15]([N:18]2[CH2:23][CH2:22][N:21]([C:24](=[O:35])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:34])([F:33])[F:32])[CH2:20][CH2:19]2)=[N:16][N:17]=1)=O)C>>[CH2:1]([NH:7][C:11]([C:13]1[S:14][C:15]([N:18]2[CH2:19][CH2:20][N:21]([C:24](=[O:35])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:34])([F:33])[F:32])[CH2:22][CH2:23]2)=[N:16][N:17]=1)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

3

Reactant 2

HCID 8102HexylamineHCID 115823885-[4-(2-Trifluoromethylbenzoyl)piperazin-1-YL]-[1,3,4]thiadiazole-2-carboxylic acid ethyl ester

Product 1

HCID 11612494HCID 11612494, compound

Procedure

Following the procedure as described in Example 3, making variations only as required to use n-hexylamine 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 (0.62 g, yield 48%). 1H NMR (300 MHz, CDCl3) δ 7.70-7.75. (m, 1H), 7.52-7.65 (m, 2H), 7.30-7.36 (m, 1H), 6.98-7.06 (m, 1H), 4.00-4.09 (m, 1H), 3.81-3.91 (m, 1H,), 3.62-3.70 (m, 2H), 3.48-3.55 (m, 2H), 3.29-3.43 (m, 4H), 1.52-1.62 (m, 2H), 1.20-1.40 (m, 6H), 0.80-0.90 (m, 3H). 13C NMR (75 MHz, CDCl3) δ 174.5, 167.6, 158.2, 156.0, 134.0, 133.9, 132.4, 129.6, 129.0, 127.0, 126.9, 121.8, 49.5, 49.0, 45.9, 40.7, 39.7, 31.4, 29.4, 26.5, 22.5, 14.0. MS (ES+) m/z 470 (M+1).

Sources & evidence

ORD record
ord-888fb3cb438b43f9804e64deff7044b9
Source dataset
uspto-grants-2011_04
Patent number
US07919496B2

Reaction notes

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