Dimethyl Sulfoxide → HCID 178519038, compound

HRID 2275628Notes

Reaction equation

HRID 2275628 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-d059973bedad4bcabafc7baded969aa6
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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