Cyanoacetic acid → HCID 59540533, compound

HRID 1677414Notes

Reaction equation

HRID 1677414 reaction equation
CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O.[C:23]([CH2:25][C:26]([OH:28])=O)#[N:24].[CH3:29][C:30]([CH3:55])([CH3:54])[C:31]([C:33]1[C:41]2[C:36](=[N:37][CH:38]=[C:39]([C:42]3[CH:47]=[CH:46][CH:45]=[C:44]([N:48]4[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]4)[CH:43]=3)[N:40]=2)[NH:35][CH:34]=1)=[O:32].C(N(C(C)C)CC)(C)C>ClCCl>[CH3:29][C:30]([CH3:55])([CH3:54])[C:31]([C:33]1[C:41]2[C:36](=[N:37][CH:38]=[C:39]([C:42]3[CH:43]=[C:44]([N:48]4[CH2:53][CH2:52][N:51]([C:26](=[O:28])[CH2:25][C:23]#[N:24])[CH2:50][CH2:49]4)[CH:45]=[CH:46][CH:47]=3)[N:40]=2)[NH:35][CH:34]=1)=[O:32]

Participants

7

Reactant 5

HCID 9740Cyanoacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 44206269HCID 44206269, compound

Product 1

HCID 59540533HCID 59540533, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dichloromethane (1 mL) was added to a mixture of EDCI (0.181 g, 0.945 mmol), HOBT monohydrate (0.128 g, 0.945 mmol), cyanoacetic acid (0.060 g, 0.71 mmol), and 2,2-Dimethyl-1-[2-(3-piperazin-1-yl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one (0.1718 g, 0.473 mmol) under argon. Diisopropylethylamine (DIPEA, 0.41 mL; 0.304 g, 2.36 mmol) was subsequently added and the reaction was stirred overnight at ambient temperature. The reaction was quenched with saturated aqueous NaHCO3 and extracted 3 times with dichloromethane. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. Preparative thin layer chromatography afforded 0.0402 g (20% yield) of 3-(4-{3-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-piperazin-1-yl)-3-oxo-propionitrile as an off-white solid.

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3
  2. extractionextracted 3 times with dichloromethane
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4c02c6a18d2e472ba31de73f4266f816
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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