Trifluoroacetate → 8-{2-[1,1-dimethyl-3-(2-oxo-5-trifluoromethyl-2,3-dihydro-benzimidazol-1-yl)-propylamino]-1-hydroxy-ethyl}-6-hydroxy-4H-benzo[1,4]oxazin-3-one

HRID 493083Notes

Reaction equation

HRID 493083 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:20]([OH:26])[CH:21](OCC)O)[C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=1)C1C=CC=CC=1.[NH2:27][C:28]([CH3:46])([CH3:45])[CH2:29][CH2:30][N:31]1[C:35]2[CH:36]=[CH:37][C:38]([C:40]([F:43])([F:42])[F:41])=[CH:39][C:34]=2[NH:33][C:32]1=[O:44].FC(F)(F)C([O-])=O>>[CH3:46][C:28]([NH:27][CH2:21][CH:20]([C:11]1[C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=[C:9]([OH:8])[CH:10]=1)[OH:26])([CH3:45])[CH2:29][CH2:30][N:31]1[C:35]2[CH:36]=[CH:37][C:38]([C:40]([F:43])([F:41])[F:42])=[CH:39][C:34]=2[NH:33][C:32]1=[O:44]

Participants

4

Reactant 3

HCID 84468TrifluoroacetateHCID 597964601-(3-Amino-3-methyl-butyl)-5-trifluoromethyl-1,3-dihydro-benzimidazol-2-oneHCID 671880306-benzyloxy-8-(2-ethoxy-1,2-dihydroxy-ethyl)-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 597964588-{2-[1,1-dimethyl-3-(2-oxo-5-trifluoromethyl-2,3-dihydro-benzimidazol-1-yl)-propylamino]-1-hydroxy-ethyl}-6-hydroxy-4H-benzo[1,4]oxazin-3-one

Procedure

Prepared according to General Method 1 from 357 mg (1 mmol) 6-benzyloxy-8-(2-ethoxy-1,2-dihydroxy-ethyl)-4H-benzo[1,4]oxazin-3-one and 287 mg (1 mmol) 1-(3-amino-3-methyl-butyl)-5-trifluoromethyl-1,3-dihydro-benzimidazol-2-one. Yield: 76 mg (13%, trifluoroacetate); mass spectroscopy: [M+H]+=495.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-399074bc54364ad2b44ac9515f1a9056
Source dataset
uspto-grants-2009_05
Patent number
US07534789B2

Reaction notes

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