Ethyl Acetate → tert-butyl {2-[(2-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino)-2-oxoacetyl)amino]ethyl}carbamate

HRID 1247817ノート

反応式

HRID 1247817 の反応式
[O:1]=[C:2](N1C=CN=C1)[C:3](N1C=CN=C1)=[O:4].[CH3:15][N:16]1[C:20]([NH:21][C:22]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:19]([NH2:41])[CH:18]=[N:17]1.[NH2:42][CH2:43][CH2:44][NH:45][C:46](=[O:52])[O:47][C:48]([CH3:51])([CH3:50])[CH3:49].C(OCC)(=O)C>CN(C)C=O>[CH3:15][N:16]1[C:20]([NH:21][C:22]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[C:19]([NH:41][C:3](=[O:4])[C:2]([NH:42][CH2:43][CH2:44][NH:45][C:46](=[O:52])[O:47][C:48]([CH3:49])([CH3:51])[CH3:50])=[O:1])[CH:18]=[N:17]1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 1004391,1'-OxalyldiimidazoleHCID 187201N-BOC-ethylenediamineHCID 685167251-methyl-N5-trityl-1H-pyrazole-4,5-diamine

生成物 1

HCID 86593408tert-butyl {2-[(2-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino)-2-oxoacetyl)amino]ethyl}carbamate収率 72.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of 1,1′-(1,2-dioxo-1,2-ethanediyl)bis-1H-imidazole (761 mg) in N,N-dimethylformamide (8 ml) was added 1-methyl-N5-trityl-1H-pyrazole-4,5-diamine (709 mg) under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added a solution of tert-butyl 2-aminoethylcarbamate (1.28 g) in N,N-dimethylformamide (2 ml), and the mixture was stirred at room temperature for 27 hours. To the reaction mixture was added ethyl acetate (50 ml). After the precipitate was filtered off, the filtrate was washed successively with water, 5% aqueous citric acid solution and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crystalline residue was washed with a mixed solvent of diethyl ether and ethyl acetate and dried in vacuo to give tert-butyl {2-[(2-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-2-oxoacetyl)amino]ethyl}carbamate (823 mg) as a solid.

後処理

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 27 hours
  3. filtrationAfter the precipitate was filtered off
  4. washthe filtrate was washed successively with water, 5% aqueous citric acid solution and brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. washThe crystalline residue was washed with a mixed solvent of diethyl ether and ethyl acetate
  9. customdried in vacuo

出典と根拠

ORDレコード
ord-1185d0e06a834749af5f3347f554930d
出典データセット
uspto-grants-2006_10
特許番号
US07129232B2

反応ノート

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