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 1851288Notes

Reaction equation

HRID 1851288 reaction equation
[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

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8471TriethylamineSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-7cef254833764c51bcb84c4d6c1f760c
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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