Dimethylformamide → HCID 58413075, compound

HRID 240630Notes

Reaction equation

HRID 240630 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[F:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[C:14]3[C:21]([CH3:22])=[C:20]([C:23]([NH2:25])=[O:24])[S:19][C:15]=3[N:16]=[CH:17][N:18]=2)=[C:8]([O:26][C@@H:27]2[CH2:32][CH2:31][CH2:30][NH:29][CH2:28]2)[CH:7]=1.C(N(CC)CC)C.CN(C=O)C>CO.CCOC(C)=O>[C:1]([CH2:2][CH2:3][N:29]1[CH2:30][CH2:31][CH2:32][C@@H:27]([O:26][C:8]2[CH:7]=[C:6]([F:5])[CH:11]=[CH:10][C:9]=2[NH:12][C:13]2[C:14]3[C:21]([CH3:22])=[C:20]([C:23]([NH2:25])=[O:24])[S:19][C:15]=3[N:16]=[CH:17][N:18]=2)[CH2:28]1)#[N:4]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7855AcrylonitrileHCID 8471TriethylamineHCID 58413095HCID 58413095, compound

Product 1

HCID 58413075HCID 58413075, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acrylonitrile (20 μl) was added to a suspension of 4-[4-fluoro-2-((R)-piperidin-3-yloxy)-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid amide (60 mg) and triethylamine (42 μl), in methanol (1 ml). After 1 h DMF (0.5 ml) was added. The reaction mixture was stirred at room temperature overnight. The reaction was diluted with EtOAc and washed with water and brine. The organic phase was passed through a hydrophobic frit and evaporated. The residue was triturated with diethylether.

Workup

  1. washwashed with water and brine
  2. customevaporated
  3. customThe residue was triturated with diethylether

Sources & evidence

ORD record
ord-c859fb2a0f48478b9bb67a51e23e620b
Source dataset
uspto-grants-2014_02
Patent number
US08648068B2

Reaction notes

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