Dimethyl Sulfoxide → HCID 178519038, compound

HRID 557914Notes

Reaction equation

HRID 557914 reaction equation
F[C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3([C:17]([N:19]4[CH2:23][CH2:22][C@@:21]5([C:27]6[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=6[C:25](=[O:32])[O:24]5)[CH2:20]4)=[O:18])[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([O-])(=[O:35])C.[NH4+].CS(C)=O.C1(O)C=CC=CC=1.NC1C=CC=CC=1>O>[OH:35][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3([C:17]([N:19]4[CH2:23][CH2:22][C@@:21]5([C:27]6[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=6[C:25](=[O:32])[O:24]5)[CH2:20]4)=[O:18])[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 996PhenolHCID 6115AnilineHCID 517165Ammonium AcetateHCID 66661906HCID 66661906, compound

Product 1

HCID 178519038HCID 178519038, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (1R)-1′-({1-[4-(6-fluoropyridin-3-yl)phenyl]cyclopropyl}carbonyl)-3H-spiro[2-benzofuran-1,3′-pyrrolidin]-3-one (20.0 mg, 0.0000467 mol, see example 250 for the preparation), and ammonium acetate (0.0216 g, 0.000280 mol) in dimethyl sulfoxide (0.5 mL, 0.007 mol) and water (0.1 mL) was heated at 100° C. in a sealed tube overnight. The major product was the phenol rather than the aniline derivative. The product was isolated and purified by prep-HPLC. LC-MS: 427.2 (M+H+)

Workup

  1. customThe product was isolated
  2. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-b83ce57f2fae4b0b8ebdd4d403545072
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

Loading…