4-Fluorobenzylamine → HCID 11663243, compound

HRID 2074141Notes

Reaction equation

HRID 2074141 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.C([O:12][C:13]([C:15]1[S:16][C:17]([N:20]2[CH2:25][CH2:24][N:23]([C:26](=[O:37])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]([F:36])([F:35])[F:34])[CH2:22][CH2:21]2)=[N:18][N:19]=1)=O)C>>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:13]([C:15]2[S:16][C:17]([N:20]3[CH2:21][CH2:22][N:23]([C:26](=[O:37])[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]([F:36])([F:35])[F:34])[CH2:24][CH2:25]3)=[N:18][N:19]=2)=[O:12])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 673264-FluorobenzylamineHCID 115823885-[4-(2-Trifluoromethylbenzoyl)piperazin-1-YL]-[1,3,4]thiadiazole-2-carboxylic acid ethyl ester

Product 1

HCID 11663243HCID 11663243, compound

Procedure

Following the procedure as described in Example 3, making variations only as required to use 4-fluorobenzylamine 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 (0.070 g, yield 50%). 1H NMR (300 MHz, CDCl3) δ 7.74-7.71 (m, 1H), 7.64-7.52 (m, 2H), 7.42-7.39 (m, 1H), 7.34-7.26 (m, 3H), 7.03-6.97 (m, 2H), 4.56 (d, J=6 Hz, 2H), 4.09-4.02 (m, 1H), 3.91-3.83 (m, 1H), 3.75-3.59 (m, 2H), 3.57-3.48 (m, 2H), 3.37-3.29 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 174.6, 167.6, 163.9, 160.6, 158.3, 155.5, 133.9, 133.3, 133.2, 132.4, 129.7, 129.5, 129.0, 126.1, 126.8, 126.7, 125.4, 121.8, 115.7, 115.4, 49.6, 48.9, 45.9, 42.9, 40.7. MS (ES+) m/z 494 (M+1).

Sources & evidence

ORD record
ord-99b018d526c9431387fed53a02edf5e3
Source dataset
uspto-grants-2011_04
Patent number
US07919496B2

Reaction notes

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