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 1851288노트

반응식

HRID 1851288 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 8471Triethylamine용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-7cef254833764c51bcb84c4d6c1f760c
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957064B2

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