Pentylamine → HCID 66584394, compound

HRID 2074148Notes

Reaction equation

CO[C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16](=[O:27])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]([F:26])([F:25])[F:24])[CH2:12][CH2:11]2)=[N:7][CH:6]=1)=[O:4].[CH2:28]([NH2:33])[CH2:29][CH2:30][CH2:31][CH3:32].[C-]#N.[Na+]>>[CH2:28]([NH:33][C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:11][CH2:12][N:13]([C:16](=[O:27])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]([F:26])([F:25])[F:24])[CH2:14][CH2:15]2)=[N:7][CH:6]=1)=[O:4])[CH2:29][CH2:30][CH2:31][CH3:32]

Participants

Reactant 3

HCID 8060Pentylamine

HCID 8929Sodium Cyanide

HCID 57659020Methyl 2-{4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl}-1,3-thiazole-5-carboxylate

Product 1

HCID 66584394HCID 66584394, compound

Procedure

A mixture of 2-[4-(2-trifluoromethylbenzoyl)piperazin-1-yl]thiazole-5-carboxylic acid methyl ester (0.317 g, 0.79 mmol), amylamine (2.0 mL) and NaCN (0.078 g, 1.59 mmol) was stirred at room temperature overnight. The title compound was obtained as a white powder after purification by column chromatography (0.207 g, 8.5% in 2 steps). m.p. 92-94° C. 1H NMR (300 MHz, CDCl3) δ 7.72 (d, J=7.5 Hz, 1H), 7.63-7.51 (m, 2H), 7.39 (s, 1H), 7.33 (d, J=7.5 Hz, 1H), 7.14-7.05 (m, 1H), 4.05-3.82 (m, 2H), 3.65-3.51 (m, 2H), 3.42-3.29 (m, 6H), 1.60-1.46 (m, 2H), 1.33-1.24 (m, 4H), 0.87 (t, J=4.2 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ 170.1, 167.5, 161.2, 146.6, 134.2, 132.3, 129.5, 127.2, 126.8, 125.4, 121.7, 112.5, 48.1, 48.0, 40.8, 39.2, 29.4, 29.1, 22.3, 14.0. MS (ES+) m/z 455.0 (M+1).

Sources & evidence

ORD record: ord-170643038b4a4279a0e599425bddd6b6
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919496B2

Reaction notes

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