Trimethylsilyl isocyanate → 4-{3-[5-Chloro-4-(4-cyclopropylcarbamoylbenzo[b]thiophen-2-yl)-pyrimidin-2-ylamino]-propyl}-piperidine-1-carboxylic acid amide

HRID 1986259Notes

Reaction equation

HRID 1986259 reaction equation
C[Si]([N:5]=[C:6]=[O:7])(C)C.[CH:8]1([NH:11][C:12]([C:14]2[C:22]3[CH:21]=[C:20]([C:23]4[C:28]([Cl:29])=[CH:27][N:26]=[C:25]([NH:30][CH2:31][CH2:32][CH2:33][CH:34]5[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]5)[N:24]=4)[S:19][C:18]=3[CH:17]=[CH:16][CH:15]=2)=[O:13])[CH2:10][CH2:9]1>CN(C=O)C.C(OCC)(=O)C>[Cl:29][C:28]1[C:23]([C:20]2[S:19][C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([C:12](=[O:13])[NH:11][CH:8]4[CH2:9][CH2:10]4)[C:22]=3[CH:21]=2)=[N:24][C:25]([NH:30][CH2:31][CH2:32][CH2:33][CH:34]2[CH2:35][CH2:36][N:37]([C:6]([NH2:5])=[O:7])[CH2:38][CH2:39]2)=[N:26][CH:27]=1

Participants

5

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 688569192-[5-Chloro-2-(3-piperidin-4-yl-propylamino)-pyrimidin-4-yl]-benzo[b]thiophene-4-carboxylic acid cyclopropylamide

Product 1

HCID 688588614-{3-[5-Chloro-4-(4-cyclopropylcarbamoylbenzo[b]thiophen-2-yl)-pyrimidin-2-ylamino]-propyl}-piperidine-1-carboxylic acid amideYield 76.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trimethylsilyl isocyanate (26 mg, 0.22 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 2 hours. The mixture is diluted with ethyl acetate (1 mL) then filtered to give the title compound as a yellow solid (43 mg). ES+(m/z) 513 (35Cl) and 515 (37Cl) [M+H].

Workup

  1. filtrationthen filtered

Sources & evidence

ORD record
ord-ad205194b4d7434eac8690636f266732
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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