Imidazole → HCID 24906239, compound

HRID 1868146Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[C:24]([F:27])([F:26])[F:25])[CH2:13][C@H:12]2[CH3:28])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[NH:37]1[CH:41]=[CH:40][N:39]=[CH:38]1>O1CCOCC1.NC[C@@H]1CCCC[C@H]1CN>[F:23][C:20]1[CH:21]=[CH:22][C:17]([N:14]2[CH2:15][CH2:16][N:11]([S:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([N:37]4[CH:41]=[CH:40][N:39]=[CH:38]4)[CH:3]=3)(=[O:10])=[O:9])[C@H:12]([CH3:28])[CH2:13]2)=[C:18]([C:24]([F:27])([F:26])[F:25])[CH:19]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A suspension of (R)-1-(3-bromophenylsulfonyl)-4-(4-fluoro-2-(trifluoromethyl)phenyl)-2-methylpiperazine (168 mg, 0.35 mmol), 1,2-trans-diaminomethylcyclohexane (2.9 mg, 0.015 mmol), K3PO4 (8.5 mmg, 0.06 mmol) and Imidazole (41 mg, 0.6 mmol) in dioxane (0.6 mL) was degassed and heated to 120° C. in a sealed tube till disappearance of starting material as monitored by LCMS. The crude reaction mixture was filtered through a pad of Celite and washed with EtOAc. The crude product was purified on SiO2 column eluted with hexanes/EtOAc to give the desired product as a white solid (123 mg, 75%). HRMS: calcd for C21H20F4N4O2S+H+, 469.13158. found (ESI-FTMS, [M+H]1+), 469.13336.

Workup

customwas degassed
customThe crude reaction mixture
filtrationwas filtered through a pad of Celite
washwashed with EtOAc
customThe crude product was purified on SiO2 column
washeluted with hexanes/EtOAc

Sources & evidence

ORD record: ord-9382926982d843d3a56d666ec4c36883
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07632838B2

Reaction notes

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