Acetic Anhydride → HCID 53358059, compound

HRID 1500774Notes

Reaction equation

HRID 1500774 reaction equation
C(N(CC)CC)C.C(O[C:12](=[O:14])[CH3:13])(=O)C.[NH:15]1[CH2:20][CH2:19][CH2:18][C@@H:17]([NH:21][C:22]2[CH:27]=[CH:26][N:25]=[C:24]([C:28]3[CH:29]=[N:30][N:31]4[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][C:32]=34)[N:23]=2)[CH2:16]1>CN(C)C1C=CN=CC=1.ClCCl>[C:12]([N:15]1[CH2:20][CH2:19][CH2:18][C@@H:17]([NH:21][C:22]2[CH:27]=[CH:26][N:25]=[C:24]([C:28]3[CH:29]=[N:30][N:31]4[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][C:32]=34)[N:23]=2)[CH2:16]1)(=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67327163HCID 67327163, compound

Product 1

HCID 53358059HCID 53358059, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (44 μL, 0.32 mmol), acetic anhydride (8.2 μL, 0.09 mmol) and N,N-dimethylpyridin-4-amine (1.2 mg, 0.01 mmol) were added to a stirred solution of 3-{4-[(3R)-piperidin-3-ylamino]pyrimidin-2-yl}pyrazolo[1,5-a]pyridine-5-carbonitrile (Preparation 7b, 40 mg, 0.06 mmol) in dichloromethane (1.5 mL) and the mixture was stirred at ambient temperature for 20 hours before being partitioned between dichloromethane and 4% aqueous sodium hydrogen carbonate solution. The organic layer was separated, washed with water and brine, dried (MgSO4) and the solvent was evaporated in vacuo. The crude product was purified by flash chromatography (100:1 to 20:1 chloroform/methanol) to give the title compound (10 mg, 44%) as a solid.

Workup

  1. custombefore being partitioned between dichloromethane and 4% aqueous sodium hydrogen carbonate solution
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated in vacuo
  6. customThe crude product was purified by flash chromatography (100:1 to 20:1 chloroform/methanol)

Sources & evidence

ORD record
ord-4620420933a644659bfeaf6534d0c69e
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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