Potassium Sodium Tartrate → N-((2-chloro-1-mesityl-6-(trifluoromethyl)-1H-imidazo[1,2-a]imidazol-5-yl)methyl)-N-(cyclopropylmethyl)propan-1-amine

HRID 1295861Notes

Reaction equation

HRID 1295861 reaction equation
[CH:1]1([CH2:4][N:5]([CH2:30][CH2:31][CH3:32])[C:6]([C:8]2[N:12]3[CH:13]=[C:14]([Cl:25])[N:15]([C:16]4[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=4[CH3:24])[C:11]3=[N:10][C:9]=2[C:26]([F:29])([F:28])[F:27])=O)[CH2:3][CH2:2]1.COCCO[AlH2-]OCCOC.[Na+].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[Cl:25][C:14]1[N:15]([C:16]2[C:17]([CH3:24])=[CH:18][C:19]([CH3:23])=[CH:20][C:21]=2[CH3:22])[C:11]2[N:12]([CH:13]=1)[C:8]([CH2:6][N:5]([CH2:4][CH:1]1[CH2:2][CH2:3]1)[CH2:30][CH2:31][CH3:32])=[C:9]([C:26]([F:27])([F:28])[F:29])[N:10]=2

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 16684438Red-AlHCID 207800092-chloro-N-(cyclopropylmethyl)-1-mesityl-N-propyl-6-(trifluoromethyl)-1H-imidazo[1,2-a]imidazole-5-carboxamide

Product 1

HCID 20780255N-((2-chloro-1-mesityl-6-(trifluoromethyl)-1H-imidazo[1,2-a]imidazol-5-yl)methyl)-N-(cyclopropylmethyl)propan-1-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 6-chloro-2-trifluoromethyl-7-(2,4,6-trimethyl-phenyl)-7H-imidazo[1,2-a]imidazole-3-carboxylic acid cyclopropylmethyl-propyl-amide (27.2 mg, 0.058 mmol) in toluene (3 mL) was added a 65% solution of Red-Al in toluene (0.10 mL, 0.320 mmol). The reaction mixture was stirred at room temperature for 14 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 Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by a reverse-phase preparative HPLC. Yield—12.8 mg (39%). LC/MS: tR=1.77 min., MS: [M+H]=453.

Workup

  1. stirringthe mixture was vigorously stirred for 30 min
  2. extractionThe crude product was extracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried with Na2SO4
  4. customThe solvent was removed under reduced pressure
  5. customthe crude product was purified by a reverse-phase preparative HPLC

Sources & evidence

ORD record
ord-7413df0788444648b15f64351289eb98
Source dataset
uspto-grants-2007_07
Patent number
US07244746B2

Reaction notes

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