HCID 16113208, compound → HCID 67538541, compound

HRID 2240950Notes

Reaction equation

HRID 2240950 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][CH2:27][CH:28]=[C:29]([F:31])[F:30])[CH:20]=2)([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([F:18])[F:17])=[CH:11][CH:10]=2)[N:3]=1>C(Cl)(Cl)Cl>[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C@@:4]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][CH2:27][CH:28]=[C:29]([F:31])[F:30])[CH:20]=2)([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([F:17])[F:18])=[CH:11][CH:10]=2)[N:3]=1

Participants

3

Reactant 1

HCID 16113208HCID 16113208, compound

Product 1

HCID 67538541HCID 67538541, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A racemic mixture of 2-amino-5-{3-[(4,4-difluorobut-3-en-1-yl)oxy]phenyl}-5-[4-(difluoromethoxy)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one was separated by chiral HPLC using column type Chiralcel AD, 2×25 cm; the mobile phase was 14% ethanol in hexane with 0.1% diethylamine at 20 mL/min to obtain the title S-isomer as a glass, identified by NMR and mass spectral analyses [mp glass; [α]D25=−31.0° (c=1% SOLUTION, CHCl3); MS (ES) m/z 436.2].

Workup

  1. customwas separated by chiral HPLC
  2. customto obtain the title S-isomer as a glass

Sources & evidence

ORD record
ord-32e6e8f780454eb0a76e6dfd72f4616d
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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