Acetyl chloride → HCID 25260786, compound

HRID 383282Notes

Reaction equation

HRID 383282 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[N:17]4[CH:18]=[CH:19][C:20]([CH:22]5[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]5)=[CH:21][C:16]4=[N:15][CH:14]=3)[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:35](Cl)(=[O:37])[CH3:36].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[N:17]4[CH:18]=[CH:19][C:20]([CH:22]5[CH2:27][CH2:26][N:25]([C:35](=[O:37])[CH3:36])[CH2:24][CH2:23]5)=[CH:21][C:16]4=[N:15][CH:14]=3)[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 252609443-(2-Phenyl-pyridin-4-yl)-7-piperidin-4-yl-imidazo[1,2-a]pyridine

Product 1

HCID 25260786HCID 25260786, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2-phenyl-pyridin-4-yl)-7-piperidin-4-yl-imidazo[1,2-a]pyridine (Ex. 1.198) (1.0 eq, 0.20 mmol, 80 mg) in CH2Cl2 (2 ml) is added triethylamine (3 eq, 0.61 mmol, 0.09 ml) and acetyl chloride (1.5 eq, 0.31 mmol, 0.02 ml) and the reaction mixture is stirred at room temperature for 2 h. The reaction mixture is poured into NaHCO3 (50 ml) and the organic phase is extracted with CH2Cl2. The combined organic layers are washed with brine, dried over MgSO4, filtered and the solvent removed in vacuo. The reaction mixture is purified by flash column chromatography eluting with 9:1 DCM/MeOH to yield 1-{4-[3-(2-phenyl-pyridin-4-yl)-imidazo[1,2-a]pyridin-7-yl]-piperidin-1-yl}-ethanone as a white solid; [M+H]+=397

Workup

  1. extractionthe organic phase is extracted with CH2Cl2
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customThe reaction mixture is purified by flash column chromatography
  7. washeluting with 9:1 DCM/MeOH

Sources & evidence

ORD record
ord-218ebf67034147b88fd35bd5e842eff8
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

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