Sodium Bicarbonate → HCID 178483849、化合物

HRID 16686

反応式

HRID 16686 の反応式
Cl.Cl.Cl.[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]([C:14]2[O:22][C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[C:15]=2[NH:23][C:24]([C@H:26]2[CH2:31][CH2:30][C@H:29]([NH:32][CH3:33])[CH2:28][CH2:27]2)=[O:25])=[O:13])=[N:9][CH:10]=1.[C:34]([O:38][C:39](CC(N)C=O)=[O:40])([CH3:37])([CH3:36])[CH3:35].C(OC(OCC)[CH2:50][CH2:51][NH2:52])C.[C:56](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]([C:14]2[O:22][C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[C:15]=2[NH:23][C:24]([C@H:26]2[CH2:31][CH2:30][C@H:29]([N:32]([CH3:56])[CH2:33][CH2:50][CH2:51][NH:52][C:39](=[O:40])[O:38][C:34]([CH3:35])([CH3:36])[CH3:37])[CH2:28][CH2:27]2)=[O:25])=[O:13])=[N:9][CH:10]=1

参加物

8

反応物 5

HCID 516892Sodium BicarbonateHCID 5210291-Amino-3,3-diethoxypropaneHCID 5049666Sodium triacetoxyborohydrideHCID 194345963-t-Butoxycarbonyl-aminopropanalHCID 178484811HCID 178484811、化合物

生成物 1

HCID 178483849HCID 178483849、化合物

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8471Triethylamine溶媒

実験手順

N-(5-Chloropyridin-2-yl)-3-({[trans-4-(methylamino)-cyclohexyl]carbonyl}amino)furo[3,2-b]pyridine-2-carboxamide trihydrochloride (300 mg) obtained in Example 119 is suspended in chloroform (7 ml). To the suspension are added 3-t-butoxycarbonyl-aminopropanal (208 mg), which can be prepared from 3-aminopropionaldehyde diethyl acetal in two steps according to the method described in a literature (Synthesis, 1994, 37) and triethylamine (334 μl) under ice-cooling, and the mixture is stirred for a few minutes. After addition of sodium triacetoxy borohydride (190 mg), the reaction solution is warmed to room temperature and stirred for 2 hours. To the reaction solution is poured saturated aqueous sodium hydrogen carbonate solution under ice-cooling, and the mixture is extracted with chloroform. The organic layer is washed successively with water and saturated brine, dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate followed by ethyl acetate/methanol=20/1) to give the title compound (291 mg).

後処理

  1. temperaturecooling
  2. stirringstirred for 2 hours
  3. temperaturecooling
  4. extractionthe mixture is extracted with chloroform
  5. washThe organic layer is washed successively with water and saturated brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent is evaporated under reduced pressure
  8. customThe resulting residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate followed by ethyl acetate/methanol=20/1)

出典と根拠

ORDレコード
ord-ac3e7add2f9e43c8bde1cac7e0d86eba
出典データセット
uspto-grants-2010_06
特許番号
US07737161B2

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