Pentane, 1-isocyanato- → HCID 11328730, compound

HRID 1689844Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

Pentylisocyanate (0.034 g, 0.30 mmol) was added slowly to a solution of [4-(5-aminopyridin-2-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)methanone (0.050 g, 0.15 mmol) in dichloromethane (2 mL) at 0° C. The mixture was stirred at 25° C. for 16 h. After removal of dichloromethane, the residue was purified by column chromatography to yield the title compound as a light purple solid (24.5 mg, 35% yield). 1H NMR (300 MHz, CDCl3) δ 7.99, 7.71, 7.58, 7.33, 6.62, 6.28, 4.69, 3.91, 3.58, 3.43, 3.28, 3.18, 1.45, 1.27, 0.88. MS (ES+) m/z 464.2 (M+1).

Workup

customAfter removal of dichloromethane
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-08c587395e36441493efe8feea049052
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153636B2

Reaction notes

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