Carbamic acid, 4-pyridinyl-, phenyl ester → HCID 59175830, compound

HRID 1807798Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:16])OC2C=CC=CC=2)=[CH:3][CH:2]=1.[NH2:17][C:18]1[CH:19]=[C:20]([CH:45]=[CH:46][CH:47]=1)[CH2:21][N:22]1[CH2:27][CH2:26][N:25]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]([OH:44])([C:40]([F:43])([F:42])[F:41])[C:36]([F:39])([F:38])[F:37])=[CH:31][CH:30]=2)[CH2:24][CH2:23]1>O1CCOCC1>[F:38][C:36]([F:37])([F:39])[C:35]([C:32]1[CH:33]=[CH:34][C:29]([CH2:28][N:25]2[CH2:24][CH2:23][N:22]([CH2:21][C:20]3[CH:19]=[C:18]([NH:17][C:8]([NH:7][C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)=[O:16])[CH:47]=[CH:46][CH:45]=3)[CH2:27][CH2:26]2)=[CH:30][CH:31]=1)([OH:44])[C:40]([F:43])([F:42])[F:41]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of phenyl pyridin-4-ylcarbamate (1.173 mmol, 251 mg) and 2-(4-((4-(3-aminobenzyl)piperazin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.782 mmol, 350 mg) in dioxane was heated in a Reactivial at 100° C. for 3 days. The reaction was then concentrated under reduced pressure. Chromatography on silica eluting with a gradient of dichloromethane to dichloromethane/methanol gave the title compound (100 mg). MS (ESI) m/z 568.5 [M+H]+

Workup

concentrationThe reaction was then concentrated under reduced pressure

Sources & evidence

ORD record: ord-46e6e1c0be9242c8bac7ccd5a5ee7df3
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357679B2

Reaction notes

Loading…