Sodium Carbonate → 2-(4-Cyanophenylaminomethyl)-1-methyl-5-[1-(2-tert.butyloxycarbonyl-azetidin-1-yl)-1-(pyrrolidin-1-yl-carbonyl)-ethyl]-benzimidazole

HRID 1067475ノート

反応式

HRID 1067475 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][C:19]([C:21]([NH2:30])([C:23]([N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[O:24])[CH3:22])=[CH:20][C:13]=3[N:12]=2)=[CH:5][CH:4]=1)#[N:2].Br[CH:32]([CH2:40][CH2:41]Br)[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][CH2:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][C:19]([C:21]([N:30]4[CH2:41][CH2:40][CH:32]4[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])([C:23]([N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[O:24])[CH3:22])=[CH:20][C:13]=3[N:12]=2)=[CH:7][CH:8]=1)#[N:2]

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 5107723tert-Butyl 2,4-dibromobutyrateHCID 181881512-(4-Cyanophenylaminomethyl)-1-methyl-5-[1-amino-1-(pyrrolidin-1-yl-carbonyl)-ethyl]-benzimidazole

生成物 1

HCID 700832612-(4-Cyanophenylaminomethyl)-1-methyl-5-[1-(2-tert.butyloxycarbonyl-azetidin-1-yl)-1-(pyrrolidin-1-yl-carbonyl)-ethyl]-benzimidazole

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
55 °C

実験手順

0.8 g (1.86 mmol) of 2-(4-cyanophenylaminomethyl)-1-methyl-5-[1-amino-1-(pyrrolidin-1-yl-carbonyl)-ethyl]-benzimidazole and 1.65 g ((5.5 mmol) of tert.butyl 2,4-dibromobutyrate are dissolved in 5 ml of ethanol, mixed with 0.2 g (1.86 mmol) of sodium carbonate and stirred under nitrogen for 30 hours at 55° C. After cooling, the white precipitate is filtered off and washed with ethanol. The filtrate is concentrated by evaporation, the residue is chromatographed on silica gel, eluting with ethyl acetate and ethyl acetate/ethanol/ammonia (20:1:0.01). The desired fractions are combined and concentrated by evaporation.

後処理

  1. temperatureAfter cooling
  2. filtrationthe white precipitate is filtered off
  3. washwashed with ethanol
  4. concentrationThe filtrate is concentrated by evaporation
  5. customthe residue is chromatographed on silica gel
  6. washeluting with ethyl acetate and ethyl acetate/ethanol/ammonia (20:1:0.01)
  7. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-cdde9183850f4850b2f6a85ea4b02431
出典データセット
uspto-grants-2001_06
特許番号
US06248770B1

反応ノート

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