Methylamine → 1-[4-(Cyano-methylamino-methyl)-thiazol-2-yl]-3-(3-fluoro-benzyl)-urea

HRID 1685055Notes

Reaction equation

HRID 1685055 reaction equation
C[Si]([C:5]#[N:6])(C)C.[F:7][C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[CH2:11][NH:12][C:13]([NH:15][C:16]1[S:17][CH:18]=[C:19]([CH:21]=O)[N:20]=1)=[O:14].[CH3:26][NH2:27]>CCO>[C:26]([CH:21]([NH:6][CH3:5])[C:19]1[N:20]=[C:16]([NH:15][C:13]([NH:12][CH2:11][C:10]2[CH:23]=[CH:24][CH:25]=[C:8]([F:7])[CH:9]=2)=[O:14])[S:17][CH:18]=1)#[N:27]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 82115Trimethylsilyl cyanide2×HCID 580550461-(3-Fluorobenzyl)-3-(4-formylthiazol-2-yl)urea

Product 1

HCID 866613041-[4-(Cyano-methylamino-methyl)-thiazol-2-yl]-3-(3-fluoro-benzyl)-urea

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Trimethylsilyl cyanide (161 μL) was added to a solution of 1-(3-fluoro-benzyl)-3-(4-formyl-thiazol-2-yl)-urea (409 mg) and MeNH2 (8 M, 0.4 mL) in (EtOH 10 mL) at 0° C. The reaction mixture was stirred at room temperature for 2 hours. The additional of 170 μL of trimethylsilyl cyanide was added to convert all starting material into the product. The product was purified by aqueous work-up and chromatography.

Workup

  1. customThe product was purified by aqueous work-up and chromatography

Sources & evidence

ORD record
ord-91009f2ed39b4e6da17847a017def14b
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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