(Formyloxy)acetonitrile → 2-{5-Chloro-2-[3-(1-formylpiperidin-4-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid cyclopropylamide

HRID 1986258Notes

Reaction equation

HRID 1986258 reaction equation
[CH:1](OCC#N)=[O:2].[CH:7]1([NH:10][C:11]([C:13]2[C:21]3[CH:20]=[C:19]([C:22]4[C:27]([Cl:28])=[CH:26][N:25]=[C:24]([NH:29][CH2:30][CH2:31][CH2:32][CH:33]5[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]5)[N:23]=4)[S:18][C:17]=3[CH:16]=[CH:15][CH:14]=2)=[O:12])[CH2:9][CH2:8]1>CN(C=O)C.C(OCC)(=O)C>[CH:7]1([NH:10][C:11]([C:13]2[C:21]3[CH:20]=[C:19]([C:22]4[C:27]([Cl:28])=[CH:26][N:25]=[C:24]([NH:29][CH2:30][CH2:31][CH2:32][CH:33]5[CH2:34][CH2:35][N:36]([CH:1]=[O:2])[CH2:37][CH2:38]5)[N:23]=4)[S:18][C:17]=3[CH:16]=[CH:15][CH:14]=2)=[O:12])[CH2:8][CH2:9]1

Participants

5

Reactant 2

HCID 4205685(Formyloxy)acetonitrileHCID 688569192-[5-Chloro-2-(3-piperidin-4-yl-propylamino)-pyrimidin-4-yl]-benzo[b]thiophene-4-carboxylic acid cyclopropylamide

Product 1

HCID 866253752-{5-Chloro-2-[3-(1-formylpiperidin-4-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid cyclopropylamideYield 74.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cyanomethyl formate (10 mg, 0.11 mmol) is added to a stirred suspension of 2-[5-chloro-2-(3-piperidin-4-yl-propylamino)-pyrimidin-4-yl]-benzo[b]thiophene-4-carboxylic acid cyclopropylamide (50 mg, 0.11 mmol) in DMF (1 mL) and stirred for 18 hours to form a thick suspension. The mixture is diluted with ethyl acetate (1 mL) then filtered to give the title compound as a solid (41 mg). ES+(m/z) 498 (35Cl) and 500 (37Cl) [M+H].

Workup

  1. customto form a thick suspension
  2. filtrationthen filtered

Sources & evidence

ORD record
ord-5ffe8d85ba204466aa5eedb631095487
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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