Piperidine → HCID 71014225, compound

HRID 716065Notes

Reaction equation

HRID 716065 reaction equation
[CH:1]([C:3]1[CH:32]=[CH:31][C:6]([NH:7][C:8]2[N:9]=[C:10]3[C:16]([C:17]([NH:19][CH:20]([CH3:22])[CH3:21])=[O:18])=[CH:15][N:14]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:11]3=[N:12][CH:13]=2)=[CH:5][CH:4]=1)=O.[O:33]1[CH2:38][CH2:37][N:36]([C:39](=[O:43])[CH2:40][C:41]#[N:42])[CH2:35][CH2:34]1.N1CCCCC1>C(Cl)Cl>[C:41]([C:40]([C:39]([N:36]1[CH2:35][CH2:34][O:33][CH2:38][CH2:37]1)=[O:43])=[CH:1][C:3]1[CH:32]=[CH:31][C:6]([NH:7][C:8]2[N:9]=[C:10]3[C:16]([C:17]([NH:19][CH:20]([CH3:22])[CH3:21])=[O:18])=[CH:15][N:14]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:28])([CH3:30])[CH3:29])[C:11]3=[N:12][CH:13]=2)=[CH:5][CH:4]=1)#[N:42]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 2292794-(Cyanoacetyl)morpholineHCID 86712132HCID 86712132, compound

Product 1

HCID 71014225HCID 71014225, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 20 ml vial 2-(4-formylanilino)-N-isopropyl-5-(2-trimethylsilylethoxymethyl)-pyrrolo[2,3-b]pyrazine-7-carboxamide (50 mg, 0.11 mmol), 3-morpholino-3-oxopropanenitrile (33.99 mg, 0.22 mmol) and piperdine (0.02 ml, 0.22 mmol) were mixed and stirred overnight. The residues was dissolved in minimum CH2Cl2, loaded on silica gel column, and eluted with EtOAc:hexane, 0, 50, 80, 100% to get 60 mg of 2-[4-(2-cyano-3-morpholino-3-oxo-prop-1-enyl)anilino]-N-isopropyl-5-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-b]pyrazine-7-carboxamide as a white solid.

Workup

  1. washeluted with EtOAc

Sources & evidence

ORD record
ord-01762aa9cd484b37b59c813bcd98b272
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

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