Cyclopropaneethanamine → HCID 11604870, compound

HRID 2074131Notes

Reaction equation

HRID 2074131 reaction equation
[CH:1]1([CH2:4][CH2:5][NH2:6])[CH2:3][CH2:2]1.C([O:9][C:10]([C:12]1[S:13][C:14]([N:17]2[CH2:22][CH2:21][N:20]([C:23](=[O:34])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]([F:33])([F:32])[F:31])[CH2:19][CH2:18]2)=[N:15][N:16]=1)=O)C>>[CH:1]1([CH2:4][CH2:5][NH:6][C:10]([C:12]2[S:13][C:14]([N:17]3[CH2:18][CH2:19][N:20]([C:23](=[O:34])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([F:33])([F:32])[F:31])[CH2:21][CH2:22]3)=[N:15][N:16]=2)=[O:9])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 10240761CyclopropaneethanamineHCID 115823885-[4-(2-Trifluoromethylbenzoyl)piperazin-1-YL]-[1,3,4]thiadiazole-2-carboxylic acid ethyl ester

Product 1

HCID 11604870HCID 11604870, compound

Procedure

Following the procedure as described in Example 3, making variations only as required to use 2-cyclopropylethylamine 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 (0.90 g, 83% yield). 1H NMR (500 MHz, CDCl3) δ 7.74 (d, J=7.8 Hz, 1H), 7.64 (dd, J=7.5, 7.5 Hz, 1H), 7.57 (dd, J=7.5, 7.5 Hz, 1H), 7.35 (d, J=7.5 Hz, 1H), 7.19 (t, J=5.8 Hz, 1H), 4.04-4.10 (m, 1H), 3.86-3.92 (m, 1H), 3.64-3.75 (m, 2H), 3.49-3.56 (m, 4H), 3.33-3.37 (m, 2H), 1.51 (dt, 2H, J=7.0, 7.0 Hz), 0.68-0.75 (m, 1H), 0.46-0.51 (m, 2H), 0.08-0.12 (m, 2H). MS (ES+) m/z 454.2 (M+1).

Sources & evidence

ORD record
ord-6cdb776051ca401baeb459a8ace65385
Source dataset
uspto-grants-2011_04
Patent number
US07919496B2

Reaction notes

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