Carbamic acid, 4-pyridinyl-, phenyl ester → HCID 59175854, compound

HRID 1807788Notes

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]1[CH:36]=[CH:35][C:34]([NH:37][C:38](=O)[O:39]C2C=CC=CC=2)=[CH:33][CH:32]=1>O1CCOCC1>[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:38]([NH:37][C:34]4[CH:35]=[CH:36][N:31]=[CH:32][CH:33]=4)=[O:39])=[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-hexafluoro-propan-2-ol (0.231 mmol, 0.1 g) and phenyl pyridin-4-ylcarbamate (0.346 mmol, 0.074 g) were combined in dioxane (1 mL) in a Reactivial and heated to 100° C. for 2 days. The reaction mixture was concentrated at reduced pressure. The resulting residue was taken up in dichloromethane, washed with water, dried over sodium sulphate and concentrated at reduced pressure. The residue was purified by silica chromatography (eluting with a solvent gradient from dichloromethane to 6% methanol/dichloromethane) to afford the title compound (43 mg). MS (ESI) m/z 555.2 [M+H]+

Workup

concentrationThe reaction mixture was concentrated at reduced pressure
washwashed with water
dry with materialdried over sodium sulphate
concentrationconcentrated at reduced pressure
customThe residue was purified by silica chromatography (
washeluting with a solvent gradient from dichloromethane to 6% methanol/dichloromethane)

Sources & evidence

ORD record: ord-03d9d6520c60432cbb1f31be616b1004
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357679B2

Reaction notes

Loading…