Acetic Acid → HCID 58011709, compound

HRID 660936Notes

Reaction equation

HRID 660936 reaction equation
[C:1]([OH:4])(=O)[CH3:2].[F:5][C:6]([F:16])([F:15])[C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH2:10][NH2:11].[CH:17]1[CH:18]=[CH:19][C:20]2N(O)N=N[C:21]=2[CH:22]=1.[CH3:27][CH2:28][N:29]=[C:30]=[N:31][CH2:32][CH2:33][CH2:34]N(C)C.[ClH:38].CN(C)C=[O:42]>O>[Cl:38][C:17]1[CH:18]=[CH:19][C:20]([C:30]2[N:31]([CH:32]3[CH2:33][CH2:34]3)[C:27](=[O:42])[N:28]([CH2:2][C:1]([NH:11][CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[C:7]([C:6]([F:15])([F:16])[F:5])[CH:8]=3)=[O:4])[CH:29]=2)=[CH:21][CH:22]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 759623-(Trifluoromethyl)benzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 58011709HCID 58011709, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

50.0 mg (0.171 mmol) of 4-(4-chlorophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetic acid from Example 130A, 32.9 mg (0.188 mmol) of 3-trifluoromethylbenzylamine and 27.7 mg (0.205 mmol) of HOBt are placed in 1.5 ml of dimethylformamide and treated with 42.6 mg (0.222 mmol) of EDC hydrochloride. This is stirred overnight at room temperature, then stirred with 19 ml of water and the resulting precipitate recovered by filtration. The crude product is washed with water and dried in vacuo. 65 mg (85% of theory) of the target compound are thus obtained.

Workup

  1. filtrationthe resulting precipitate recovered by filtration
  2. washThe crude product is washed with water
  3. customdried in vacuo
  4. custom65 mg (85% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-ed65f2f67f75434e953024ba85c5a17b
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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