Triethylamine → 1-Trityl-1H-imidazole-4-carboxylic acid 4-[4-(3,3-dimethyl-butyryl)-3-hydroxy-2-trifluoromethyl-phenoxymethyl]-benzylamide

HRID 2355293Notes

Reaction equation

HRID 2355293 reaction equation
O.ON1C2C=CC=CC=2N=N1.[C:12]([N:31]1[CH:35]=[C:34]([C:36]([OH:38])=O)[N:33]=[CH:32]1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl.CN(C)CCCN=C=NCC.Cl.[NH2:52][CH2:53][C:54]1[CH:79]=[CH:78][C:57]([CH2:58][O:59][C:60]2[CH:65]=[CH:64][C:63]([C:66](=[O:72])[CH2:67][C:68]([CH3:71])([CH3:70])[CH3:69])=[C:62]([OH:73])[C:61]=2[C:74]([F:77])([F:76])[F:75])=[CH:56][CH:55]=1.C(N(CC)CC)C>C(#N)C>[CH3:69][C:68]([CH3:71])([CH3:70])[CH2:67][C:66]([C:63]1[CH:64]=[CH:65][C:60]([O:59][CH2:58][C:57]2[CH:78]=[CH:79][C:54]([CH2:53][NH:52][C:36]([C:34]3[N:33]=[CH:32][N:31]([C:12]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:35]=3)=[O:38])=[CH:55][CH:56]=2)=[C:61]([C:74]([F:75])([F:76])[F:77])[C:62]=1[OH:73])=[O:72]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 105701171-Trityl-1H-imidazole-4-carboxylic acidHCID 671763671-[4-(4-Aminomethyl-benzyloxy)-2-hydroxy-3-trifluoromethyl-phenyl]-3,3-dimethyl-butan-1-one hydrochloride

Product 1

HCID 671761011-Trityl-1H-imidazole-4-carboxylic acid 4-[4-(3,3-dimethyl-butyryl)-3-hydroxy-2-trifluoromethyl-phenoxymethyl]-benzylamideYield 86.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Add 1-hydroxybenzotriazole hydrate (63.8 mg; 417 μmol), 1-trityl-1H-imidazole-4-carboxylic acid (148 mg, 417 μmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (79.9 mg, 417 μmol) to anhydrous acetonitrile (7 mL). Stir the reaction mixture at room temperature for 1 hr. Then add 1-[4-(4-aminomethyl-benzyloxy)-2-hydroxy-3-trifluoromethyl-phenyl]-3,3-dimethyl-butan-1-one hydrochloride (150 mg, 347 μmol) and triethylamine (97 μL, 695 μmol). Stir the reaction mixture at room temperature overnight. Quench the reaction with water and the solid, filter the solid and dry to give the title compound (220 mg, 301 μmol). MS (m/z): 730 (M−1).

Workup

  1. stirringStir the reaction mixture at room temperature overnight
  2. customQuench
  3. customthe reaction with water
  4. filtrationthe solid, filter the solid
  5. customdry

Sources & evidence

ORD record
ord-0b691430937f4d4f8411f80d38d4e078
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

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