Formic Acid → HCID 66697189, compound

HRID 2386796Notes

Reaction equation

[CH2:1]([O:3][C:4](=O)[CH3:5])C.[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].[Li+].[OH-].[CH:37]([OH:39])=[O:38]>CN(C1C=CN=CC=1)C.C(#N)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:7][C:8]1[CH:13]=[C:12]([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:18])([F:19])[F:20])[O:14][C:8]1[CH:13]=[C:4]([CH:5]=[CH:10][CH:9]=1)[O:3][CH2:1][C:37]([OH:39])=[O:38]

Participants

Conditions

Temperature: 80 °C

Procedure

Copper(II)acetate (39 mg), 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-acetic acid ethyl ester (CAS Reg. No. 850411-07-3, 66 mg), and DMAP (44 mg) were 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, 30 mg) in acetonitrile (3 ml). The mixture was stirred with molecular sieves under air atmosphere for 5 h at 80° C. Aqueous 1N LiOH solution was added, and the mixture stirred for 1 h. 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 (32 mg) as a white solid. MS (m/e)=565.2 [M+H+].

Workup

stirringthe mixture stirred for 1 h
custompurified by prep

Sources & evidence

ORD record: ord-7ae88a62570f40d3833fb079f52a96dd
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268820B2

Reaction notes

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