Formic Acid → HCID 66697334, compound

HRID 2096809Notes

Reaction equation

HRID 2096809 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:9]=1[CH:15]([CH3:34])[C:16]([C:22]1[CH:33]=[CH:32][C:25]2[N:26]([CH3:31])[C:27](=[O:30])[N:28]([CH3:29])[C:24]=2[CH:23]=1)([OH:21])[C:17]([F:20])([F:19])[F:18].Cl[C:36]1[N:45]=[CH:44][C:43]([Cl:46])=[CH:42][C:37]=1[C:38]([O:40][CH3:41])=[O:39].C(O)=O>CN(C=O)C>[CH3:41][O:40][C:38](=[O:39])[C:37]1[CH:42]=[C:43]([Cl:46])[CH:44]=[N:45][C:36]=1[O:14][C:12]1[CH:11]=[CH:10][C:9]([CH:15]([CH3:34])[C:16]([C:22]2[CH:33]=[CH:32][C:25]3[N:26]([CH3:31])[C:27](=[O:30])[N:28]([CH3:29])[C:24]=3[CH:23]=2)([OH:21])[C:17]([F:18])([F:19])[F:20])=[C:8]([Cl:7])[CH:13]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 2764318Methyl 2,5-DichloronicotinateHCID 23665647Potassium tert-butoxideHCID 59507321HCID 59507321, compound

Product 1

HCID 66697334HCID 66697334, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium tert-butoxide (6 mg) was added to a solution of 5-[2-(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1,3-dimethyl-1,3-dihydro-benzoimidazol-2-one (Example 85, 20 mg) in DMF (3.6 ml). The solution was added to methyl 2,5-dichloronicotinate (CAS Reg. No. 67754-03-4, 20 mg). The resulting mixture was stirred overnight at room temperature. The mixture was acidified with HCOOH and purified by prep. HPLC (C18-column, solvent gradient 20-98% CH3CN in 0.1% HCOOH[aq]) to give the title compound (10 mg). MS (m/e)=584.3 [M+H+].

Workup

  1. custompurified by prep

Sources & evidence

ORD record
ord-e59b43e3217b41f6b40949534b314b0d
Source dataset
uspto-grants-2013_05
Patent number
US08450313B2

Reaction notes

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