2,5-Dioxopyrrolidin-1-yl 2-cyanoacetate → HCID 67959096, compound

HRID 2279066Notes

Reaction equation

HRID 2279066 reaction equation
O=C1CCC(=O)N1[O:8][C:9](=O)[CH2:10][C:11]#[N:12].[CH3:14][O:15][C:16]1[C:21]([C:22]2[N:26]3[N:27]=[C:28]([NH:31][C@@H:32]4[CH2:37][CH2:36][CH2:35][NH:34][CH2:33]4)[CH:29]=[CH:30][C:25]3=[N:24][CH:23]=2)=[CH:20][CH:19]=[CH:18][N:17]=1>ClCCl>[CH3:14][O:15][C:16]1[C:21]([C:22]2[N:26]3[N:27]=[C:28]([NH:31][C@@H:32]4[CH2:37][CH2:36][CH2:35][N:34]([C:9](=[O:8])[CH2:10][C:11]#[N:12])[CH2:33]4)[CH:29]=[CH:30][C:25]3=[N:24][CH:23]=2)=[CH:20][CH:19]=[CH:18][N:17]=1

Participants

4

Reactant 2

HCID 534158962,5-Dioxopyrrolidin-1-yl 2-cyanoacetateHCID 67959033HCID 67959033, compound

Product 1

HCID 67959096HCID 67959096, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[(2,5-Dioxopyrrolidin-1-yl)oxy]-3-oxopropanenitrile (prepared as described in BE875054(A1), 75 mg, 0.23 mmol) was added to a stirred solution of 3-(2-methoxy pyridin-3-yl)-N-[(3R)-piperidin-3-yl]imidazo[1,2-b]pyridazin-6-amine (Preparation 3b, 63 mg, 0.35 mmol) in dichloromethane (4 mL) and the mixture was stirred at ambient temperature for 18 hours. The solvent was then removed under reduced pressure and the residue was purified by flash chromatography (100% ethyl acetate to 3:2 ethyl acetate/ethanol) to give the title compound (58 mg, 64%) as a solid.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customthe residue was purified by flash chromatography (100% ethyl acetate to 3:2 ethyl acetate/ethanol)

Sources & evidence

ORD record
ord-fcdb01bb8f2d454bb1d22370f8147805
Source dataset
uspto-grants-2015_09
Patent number
US09133200B2

Reaction notes

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