Ethyl 4-isocyanatobenzoate → HCID 59175898, compound

HRID 1807789Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([OH:30])([C:26]([F:29])([F:28])[F:27])[C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[N:31]([C:34]1[CH:44]=[CH:43][C:37]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:36][CH:35]=1)=[C:32]=[O:33]>ClCCl>[F:27][C:26]([F:29])([F:28])[C:21]([C:18]1[CH:17]=[CH:16][C:15]([CH2:14][N:11]2[CH2:10][CH2:9][N:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:32](=[O:33])[NH:31][C:34]4[CH:44]=[CH:43][C:37]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:36][CH:35]=4)=[CH:7][CH:6]=3)[CH2:13][CH2:12]2)=[CH:20][CH:19]=1)([OH:30])[C:22]([F:23])([F:24])[F:25]

Participants

Conditions

Temperature: 100 °C

Procedure

2-(4-((4-(4-Aminophenyl)piperazin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.461 mmol, 200 mg) and ethyl 4-isocyanatobenzoate (0.554 mmol, 0.060 mL, 106 mg) were combined in dichloromethane and heated in a microwave at 100° C. for 10 minutes. The reaction mixture was concentrated under vacuum. The residue was purified by acidic preparative HPLC and SCX chromatography to afford the title compound (212.3 mg). MS (ESI) m/z 625.2 [M+H]+

Workup

concentrationThe reaction mixture was concentrated under vacuum
customThe residue was purified by acidic preparative HPLC and SCX chromatography

Sources & evidence

ORD record: ord-768c10f893104b929e52f6812e6b8e47
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357679B2

Reaction notes

Loading…