Butylamine → HCID 11517830, compound

HRID 2074135Notes

Reaction equation

HRID 2074135 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].C([O:8][C:9]([C:11]1[S:12][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:22](=[O:33])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]([F:32])([F:31])[F:30])[CH2:18][CH2:17]2)=[N:14][N:15]=1)=O)C>>[CH2:1]([NH:5][C:9]([C:11]1[S:12][C:13]([N:16]2[CH2:17][CH2:18][N:19]([C:22](=[O:33])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]([F:32])([F:31])[F:30])[CH2:20][CH2:21]2)=[N:14][N:15]=1)=[O:8])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 8007ButylamineHCID 115823885-[4-(2-Trifluoromethylbenzoyl)piperazin-1-YL]-[1,3,4]thiadiazole-2-carboxylic acid ethyl ester

Product 1

HCID 11517830HCID 11517830, compound

Procedure

Following the procedure as described in Example 3, making variations only as required to use n-butylamine 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 (0.042 g, yield 79%). 1H NMR (300 MHz, CDCl3) δ 7.72-7.69 (m, 1H), 7.63-7.49 (m, 2H), 7.33-7.3 (m, 1H), 7.03 (m, 1H), 4.08-3.8 (m, 1H), 3.9-3.8 (m, 1H), 3.68-3.62 (m, 2H), 3.54-3.47 (m, 2H), 3.42-3.35 (m, 2H), 3.33-3.28 (m, 2H), 1.6-1.5 (m, 2H), 1.42-1.3 (m, 2H), 0.9 (t, J=7.5 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ 174.5, 167.5, 158.2, 155.9, 133.9, 132.4, 129.6, 127.1, 126.9, 126.8, 126.3, 125.4, 121.7, 49.5, 48.9, 45.9, 40.7, 39.4, 31.5, 19.9, 13.6. MS (ES+) m/z 442 (M+1).

Sources & evidence

ORD record
ord-2d8ed9540e3d4f28956f2d2ee83c671f
Source dataset
uspto-grants-2011_04
Patent number
US07919496B2

Reaction notes

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