Isohexylamine → HCID 11712492, compound

HRID 2074136Notes

Reaction equation

HRID 2074136 reaction equation
[CH3:1][CH:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH2:6].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>>[CH3:1][CH:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH:6][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]

Participants

3

Reactant 2

HCID 219608IsohexylamineHCID 115823885-[4-(2-Trifluoromethylbenzoyl)piperazin-1-YL]-[1,3,4]thiadiazole-2-carboxylic acid ethyl ester

Product 1

HCID 11712492HCID 11712492, compound

Procedure

Following the procedure as described in Example 3, making variations only as required to use 4-methylpentylamine 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 (0.045 g, yield 79%). 1H NMR (300 MHz, CDCl3) δ 7.73-7.7 (m, 1H), 7.64-7.5 (m, 2H), 7.34-7.32 (m, 1H), 7.06 (br., t, 1H), 4.09-3.8 (m, 1H), 3.93-3.81 (m, 1H), 3.75-3.6 (m, 2H), 3.56-3.48 (m, 2H), 3.43-3.29 (m, 4H), 1.63-1.48 (m, 3H), 1.46-1.16 (m, 2H), 0.85 (d, J=6.6 Hz, 6H). 13C NMR (75 MHz, CDCl3) δ 174.5, 167.5, 158.2, 156.0, 133.9, 132.3, 129.6, 126.9, 126.8, 126.7, 125.3, 121.7, 49.5, 48.9, 45.9, 40.7, 39.9, 35.9, 27.7, 27.3, 22.4. MS (ES+) m/z 470 (M+1).

Sources & evidence

ORD record
ord-7867b5d4dcd7465896fa2080fec8b047
Source dataset
uspto-grants-2011_04
Patent number
US07919496B2

Reaction notes

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