1-Hydroxybenzotriazole → Rac-2-[4-(4-bromophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1h-imidazol-1-yl]-n-{1-[3-(trifluoromethyl)phenyl]ethyl}acetamide

HRID 660935Notes

Reaction equation

HRID 660935 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:18]3[CH2:20][CH2:19]3)[C:10](=[O:17])[N:11]([CH2:13][C:14]([OH:16])=O)[CH:12]=2)=[CH:4][CH:3]=1.[F:21][C:22]([F:33])([F:32])[C:23]1[CH:24]=[C:25]([CH:29]([NH2:31])[CH3:30])[CH:26]=[CH:27][CH:28]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C)C=O.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH:18]3[CH2:20][CH2:19]3)[C:10](=[O:17])[N:11]([CH2:13][C:14]([NH:31][CH:29]([C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([C:22]([F:21])([F:32])[F:33])[CH:24]=3)[CH3:30])=[O:16])[CH:12]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2782448(1R)-1-(3-(Trifluoromethyl)phenyl)ethylamineHCID 58011674[4-(4-bromophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetic acid

Product 1

HCID 58011855Rac-2-[4-(4-bromophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1h-imidazol-1-yl]-n-{1-[3-(trifluoromethyl)phenyl]ethyl}acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

40.0 mg (0.119 mmol) of 4-(4-bromophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetic acid from Example 129A, 24.7 mg (0.130 mmol) of 1-[3-(trifluoromethyl)phenyl]ethylamine and 19.2 mg (0.142 mmol) of HOBt are placed in 1.5 ml of dimethylformamide and treated with 29.6 mg (0.154 mmol) of EDC hydrochloride. This is stirred overnight at room temperature, then stirred with 15 ml of water, and the resulting precipitate is isolated and this crude product purified by preparative HPLC [Method 13]. 23 mg (38% of theory) of the target compound are thus obtained.

Workup

  1. customthe resulting precipitate is isolated
  2. customthis crude product purified by preparative HPLC [Method 13]
  3. custom23 mg (38% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-6bc37fe3821743df9b9adbe5f3f215a4
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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