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

HRID 1851284Notes

Reaction equation

HRID 1851284 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.[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

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride2×HCID 211980262-(Piperidin-4-yl)quinoxalineHCID 866306554-(6-Phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

Product 1

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

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 8471TriethylamineSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-94ff27f56df640919a32a303f18544da
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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