Sodium Bicarbonate → 2-{1-[4-(2-Cyclopropyl-6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)-benzyl]-piperidine-4-yl}-quinoxaline

HRID 1851288ノート

反応式

HRID 1851288 の反応式
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:16]=[N:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH2:3][CH2:2]1.[CH:17]1([C:20]2[N:42]=[C:23]3[N:24]=[C:25]([C:34]4[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=4)[C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:27][N:22]3[N:21]=2)[CH2:19][CH2:18]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>CN1C(=O)CCC1.C(O)(=O)C.C(N(CC)CC)C>[CH:17]1([C:20]2[N:42]=[C:23]3[N:24]=[C:25]([C:34]4[CH:41]=[CH:40][C:37]([CH2:38][N:1]5[CH2:2][CH2:3][CH:4]([C:7]6[CH:16]=[N:15][C:14]7[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=7)[N:8]=6)[CH2:5][CH2:6]5)=[CH:36][CH:35]=4)[C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:27][N:22]3[N:21]=2)[CH2:18][CH2:19]1

参加物

8

反応物 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 211980262-(Piperidin-4-yl)quinoxalineHCID 867030274-(2-Cyclopropyl-6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

生成物 1

HCID 687526902-{1-[4-(2-Cyclopropyl-6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)-benzyl]-piperidine-4-yl}-quinoxaline収率 49.7%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 8471Triethylamine溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

125.3 mg (0.59 mmol) 2-Piperidine-4-ylquinoxaline are dissolved in 5.2 mL NMP. After addition of 0.2 mL triethylamine the reaction mixture is stirred for one hour. 200 mg (0.59 mmol) 4-(2-cyclopropyl-6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde (intermediate example 4.0) and 0.06 mL acetic acid are added. The reaction mixture is stirred overnight at room temperature. 137 mg (0.65 mmol) NaBH(OAc)3, are added in portions and the reaction mixture is stirred at room temperature for four hours. Saturated NaHCO3 is added to the reaction mixture, the precipitate is filtered off and purified by chromatography on silica gel (dichloromethane/methanol). 157.8 mg (47.5%) of the pure product are obtained.

後処理

  1. stirringThe reaction mixture is stirred overnight at room temperature
  2. stirringthe reaction mixture is stirred at room temperature for four hours
  3. filtrationthe precipitate is filtered off
  4. custompurified by chromatography on silica gel (dichloromethane/methanol)

出典と根拠

ORDレコード
ord-7cef254833764c51bcb84c4d6c1f760c
出典データセット
uspto-grants-2015_02
特許番号
US08957064B2

反応ノート

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