Formic Acid → HCID 66697335, compound

HRID 2386791Notes

Reaction equation

HRID 2386791 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:28])[C:10]([C:16]1[CH:27]=[CH:26][C:19]2[N:20]([CH3:25])[C:21](=[O:24])[N:22]([CH3:23])[C:18]=2[CH:17]=1)([OH:15])[C:11]([F:14])([F:13])[F:12].[F:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][C:37]=1F)[C:33]#[N:34].C([O-])([O-])=O.[Cs+].[Cs+].C(O)=O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[CH:9]([CH3:28])[C:10]([C:16]1[CH:27]=[CH:26][C:19]2[N:20]([CH3:25])[C:21](=[O:24])[N:22]([CH3:23])[C:18]=2[CH:17]=1)([OH:15])[C:11]([F:12])([F:13])[F:14])[O:8][C:37]1[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][C:30]=1[F:29]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 10796Cesium carbonateHCID 5872033,4-DifluorobenzonitrileHCID 59507321HCID 59507321, compound

Product 1

HCID 66697335HCID 66697335, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-[2-(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1,3-dimethyl-1,3-dihydro-benzoimidazol-2-one (Example 85, 25 mg), 3,4-difluorobenzonitrile (CAS Reg. No. 64248-62-0, 10 mg), and Cs2CO3 (59 mg) in DMF (1 ml) was heated in a microwave oven at 120° C. for 30 min. The mixture was acidified with HCOOH and then purified by prep. HPLC (C18-column, solvent gradient 30-98%) to give the title compound (19 mg) as a colorless oil. MS (m/e)=534.1 [M+H+].

Workup

  1. custompurified by prep

Sources & evidence

ORD record
ord-fbdc97a2124c4febb58ddda78f736a6b
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

Loading…