Methanamine, N-methoxy-, hydrochloride (1:1) → 2-(3-(3,4-dichlorobenzyl)ureido)-N-methoxy-N-methylthiazole-4-carboxamide

HRID 1685029Notes

Reaction equation

HRID 1685029 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:5][NH:6][C:7](=[O:17])[NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([OH:16])=O)[N:13]=1.CCN(C(C)C)C(C)C.CN([C:34]([O:38][N:39]1N=NC2C=CC=C[C:40]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.CNOC>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:5][NH:6][C:7](=[O:17])[NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([N:39]([O:38][CH3:34])[CH3:40])=[O:16])[N:13]=1

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 866227642-(3-(3,4-Dichlorobenzyl)ureido)thiazole-4-carboxylic acid

Product 1

HCID 866612922-(3-(3,4-dichlorobenzyl)ureido)-N-methoxy-N-methylthiazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.58 g of 2-(3-(3,4-dichlorobenzyl)ureido)thiazole-4-carboxylic acid was dissolved in 15 ml of DMF and 3.0 eq. of DIEA and 1.05 eq. of TBTU was added. To the mixture, 1.2 eq. of N,O-dimethylhydroxylamine HCl salt was added and the reaction was stirred at room temp. overnight. The product was precipitated from water, filtered, washed with water and dried to give 2-(3-(3,4-dichlorobenzyl)ureido)-N-methoxy-N-methylthiazole-4-carboxamide.

Workup

  1. customThe product was precipitated from water
  2. filtrationfiltered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-5737823b065c4384a77e1094d9ebb7e8
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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