HCID 45488111, compound → HCID 52946950, compound

HRID 643482Notes

Reaction equation

HRID 643482 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]3[C:27]([F:32])=[N:28][CH:29]=[CH:30][CH:31]=3)[CH:21]=2)([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)[N:3]=1>CO>[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C@:4]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]3[C:27]([F:32])=[N:28][CH:29]=[CH:30][CH:31]=3)[CH:21]=2)([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:18])([F:17])[F:19])=[CH:11][CH:10]=2)[N:3]=1

Participants

3

Reactant 1

HCID 45488111HCID 45488111, compound

Product 1

HCID 52946950HCID 52946950, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A racemic mixture of 2-amino-5-[3-(2-fluoropyridin-3-yl)phenyl]-3-methyl-5-[4-(trifluoromethoxy)phenyl]-3,5-dihydro-4H-imidazol-4-one was separated by chiral HPLC using Chiralcel AD, 2×25 cm (column) with mobile phase 9% EtOH in hexanes (0.1% diethylamine) to give the title R-isomer: [α]25=−13.4 (1% in MeOH); 1H NMR (DMSOd6 300 MHz) δ 2.95 (s, 3H), 6.65 (brs, 2H), 7.28 (d, 2H), 7.4-7.45 (m, 3H), 7.5 (m, 1H), 7.55 (d, 2H), 7.65 (d, 1H), 7.95-8.0 (m, 1H), 8.2 (m, 1H); MS m/e (M+H)+ 445.

Workup

  1. customwas separated by chiral HPLC
  2. customto give the title R-isomer

Sources & evidence

ORD record
ord-79e597a1cefd4889a953fb3940cf87e5
Source dataset
uspto-grants-2010_04
Patent number
US07700602B2

Reaction notes

Loading…