Sodium Bicarbonate → 2-{1-[4-(6-Phenyl-imidazo[1,2-a]pyrimidin-7-yl)-benzyl]-piperidine-4-yl}-quinoxaline

HRID 1851284노트

반응식

HRID 1851284 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.[C:17]1([C:23]2[C:24]([C:32]3[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=3)=[N:25][C:26]3[N:27]([CH:29]=[CH:30][N:31]=3)[CH:28]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH: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>[C:17]1([C:23]2[C:24]([C:32]3[CH:33]=[CH:34][C:35]([CH2:36][N:1]4[CH2:2][CH2:3][CH:4]([C:7]5[CH:16]=[N:15][C:14]6[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=6)[N:8]=5)[CH2:5][CH2:6]4)=[CH:38][CH:39]=3)=[N:25][C:26]3[N:27]([CH:29]=[CH:30][N:31]=3)[CH:28]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

8

반응물 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride2회HCID 211980262-(Piperidin-4-yl)quinoxalineHCID 866306554-(6-Phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

생성물 1

HCID 687517372-{1-[4-(6-Phenyl-imidazo[1,2-a]pyrimidin-7-yl)-benzyl]-piperidine-4-yl}-quinoxaline

시약·촉매·용매 3

HCID 176Acetic Acid용매2회HCID 8471Triethylamine용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

195 mg (0.6 mmol) 2-Piperidine-4-ylquinoxaline are dissolved in 4.9 mL NMP. After addition of 0.19 mL triethylamine the reaction mixture is stirred for one hour. 170 mg (0.57 mmol) 4-(6-Phenyl-imidazo[1,2-a]pyrimidin-7-yl)-benzaldehyde (intermediate example 1.0) and 0.06 mL acetic acid are added. The reaction mixture is stirred overnight at room temperature. 132 mg (0.63 mmol) NaBH(OAc)3, are added in portions and the reaction mixture is stirred at room temperature for 18 hours. Additionally 75 mg NaBH(OAc)3 and 0.03 mL acetic acid are added and the stirring is continued for 23 hours. The reaction mixture is treated with saturated NaHCO3 and stirred vigorously for one hour. The precipitate is filtered off, washed with water and dried. After chromatography of the precipitate on silica gel (dichloromethane/methanol) 127.4 mg (45.2%) of the pure product are obtained. Another 66.1 mg (23.4%) of slightly contaminated product are obtained.

후처리

  1. stirringThe reaction mixture is stirred overnight at room temperature
  2. stirringthe reaction mixture is stirred at room temperature for 18 hours
  3. waitthe stirring is continued for 23 hours
  4. stirringstirred vigorously for one hour
  5. filtrationThe precipitate is filtered off
  6. washwashed with water
  7. customdried
  8. customAfter chromatography of the precipitate on silica gel (dichloromethane/methanol) 127.4 mg (45.2%) of the pure product are obtained
  9. customAnother 66.1 mg (23.4%) of slightly contaminated product are obtained

출처 및 근거

ORD 기록
ord-94ff27f56df640919a32a303f18544da
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957064B2

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