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

HRID 1246317

反応式

HRID 1246317 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒3 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e829fa74de1949ca842442fd11cf435d
出典データセット
uspto-grants-2006_10
特許番号
US07125990B2

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