Potassium Sodium Tartrate → 2-chloro-N-(cyclopropylmethyl)-1-mesityl-N-propyl-6-(trifluoromethyl)-1H-imidazo[1,2-a]imidazole-5-carboxamide

HRID 1293088

Reaction equation

HRID 1293088 reaction equation
[CH:1]1([CH2:4][NH:5][CH2:6][CH2:7][CH3:8])[CH2:3][CH2:2]1.C[Al](C)C.C([O:15][C:16]([C:18]1[N:22]2[CH:23]=[C:24]([Cl:35])[N:25]([C:26]3[C:31]([CH3:32])=[CH:30][C:29]([CH3:33])=[CH:28][C:27]=3[CH3:34])[C:21]2=[N:20][C:19]=1[C:36]([F:39])([F:38])[F:37])=O)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[CH:1]1([CH2:4][N:5]([CH2:6][CH2:7][CH3:8])[C:16]([C:18]2[N:22]3[CH:23]=[C:24]([Cl:35])[N:25]([C:26]4[C:27]([CH3:34])=[CH:28][C:29]([CH3:33])=[CH:30][C:31]=4[CH3:32])[C:21]3=[N:20][C:19]=2[C:36]([F:38])([F:37])[F:39])=[O:15])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 9357Potassium Sodium TartrateHCID 117787Cyclopropanemethanamine, N-propyl-HCID 16682925TrimethylaluminumHCID 207802236-Chloro-2-trifluoromethyl-7-(2,4,6-trimethyl-phenyl)-7H-imidazo[1,2-a]imidazole-3-carboxylic Acid Ethyl Ester

Product 1

HCID 207800092-chloro-N-(cyclopropylmethyl)-1-mesityl-N-propyl-6-(trifluoromethyl)-1H-imidazo[1,2-a]imidazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

To a solution of N-cyclopropylmethylpropylamine (0.22 mL, 1.530 mmol) in toluene (1.5 mL) at 0° C. was added 2.0M solution of trimethylaluminum in toluene (0.77 mL, 1.530 mmol). The clear solution was warmed to room temperature and stirred for 1 h. A solution of 6-chloro-2-trifluoromethyl-7-(2,4,6-trimethyl-phenyl)-7H-imidazo[1,2-a]imidazole-3-carboxylic acid ethyl ester (37.7 mg, 0.094 mmol) in toluene (1.0 mL) was added at 0° C. via cannula. The reaction mixture was heated at 80° C. for 2 h. A solution of Rochelle's salt (2.0 mL) was added carefully at 0° C. and the mixture was vigorously stirred for 30 min. The crude product was extracted with ethyl acetate. The combined organic extracts were dried with MgSO4. The solvent was removed under reduced pressure and the crude product was purified by a reverse-phase preparative HPLC. Yield—39.5 mg (90%). LC/MS: tR=1.93 min., MS: [M+H]=467.

Workup

  1. temperatureThe reaction mixture was heated at 80° C. for 2 h
  2. stirringthe mixture was vigorously stirred for 30 min
  3. extractionThe crude product was extracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried with MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customthe crude product was purified by a reverse-phase preparative HPLC

Sources & evidence

ORD record
ord-d25d13ec0289413b8fa2c5b7481787e0
Source dataset
uspto-grants-2007_07
Patent number
US07238699B2

Linked notes

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