3-[(2,5-Dioxopyrrolidin-1-yl)oxy]-3-oxopropanenitrile → HCID 53358058, compound

HRID 1500773Notes

Reaction equation

HRID 1500773 reaction equation
O=C1CCC(=O)N1[O:8][C:9](=O)[CH2:10][C:11]#[N:12].[NH:14]1[CH2:19][CH2:18][CH2:17][C@@H:16]([NH:20][C:21]2[CH:26]=[CH:25][N:24]=[C:23]([C:27]3[CH:28]=[N:29][N:30]4[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][C:31]=34)[N:22]=2)[CH2:15]1>C(O)C>[C:11]([CH2:10][C:9]([N:14]1[CH2:19][CH2:18][CH2:17][C@@H:16]([NH:20][C:21]2[CH:26]=[CH:25][N:24]=[C:23]([C:27]3[CH:28]=[N:29][N:30]4[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][C:31]=34)[N:22]=2)[CH2:15]1)=[O:8])#[N:12]

Participants

4

Reactant 2

HCID 534158963-[(2,5-Dioxopyrrolidin-1-yl)oxy]-3-oxopropanenitrileHCID 67327163HCID 67327163, compound

Product 1

HCID 53358058HCID 53358058, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-[(2,5-Dioxopyrrolidin-1-yl)oxy]-3-oxopropanenitrile (prepared as described in BE875054(A1), 40 mg, 0.20 mmol) was added to a stirred solution of 3-{4-[(3R)-piperidin-3-ylamino]pyrimidin-2-yl}pyrazolo[1,5-a]pyridine-5-carbonitrile (Preparation 7b, 60 mg, 0.16 mmol) in ethanol (1.2 mL) and the mixture was stirred at ambient temperature for 20 hours. The solvent was then removed under reduced pressure and the residue was taken-up in a mixture of dichloromethane and 4% aqueous sodium hydrogen carbonate solution. The organic layer was separated, dried (MgSO4) and the solvent evaporated in vacuo. The crude product was purified by flash chromatography (chloroform to 40:1 chloroform/methanol) to give the title compound (20 mg, 27%) as a solid.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. additionthe residue was taken-up in a mixture of dichloromethane and 4% aqueous sodium hydrogen carbonate solution
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customthe solvent evaporated in vacuo
  6. customThe crude product was purified by flash chromatography (chloroform to 40:1 chloroform/methanol)

Sources & evidence

ORD record
ord-5beee8e2a4e94398b60f8efd0cf80120
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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