Dimethylformamide → 2-(3-(3,4-Dichlorobenzyl)ureido)-N-(2-methoxyethyl)-N-methylthiazole-4-carboxamide

HRID 1020266Notes

Reaction equation

HRID 1020266 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH3:6].CN(C=O)C.[Cl:12][C:13]1[CH:14]=[C:15]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:16][NH:17][C:18](=[O:28])[NH:19][C:20]1[S:21][CH:22]=[C:23]([C:25]([OH:27])=O)[N:24]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CCOC(C)=O.C(N(CC)CC)C>[Cl:12][C:13]1[CH:14]=[C:15]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:16][NH:17][C:18](=[O:28])[NH:19][C:20]1[S:21][CH:22]=[C:23]([C:25]([N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH3:6])=[O:27])[N:24]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 300977(2-Methoxyethyl)(methyl)amineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 866227642-(3-(3,4-Dichlorobenzyl)ureido)thiazole-4-carboxylic acid

Product 1

HCID 250522152-(3-(3,4-Dichlorobenzyl)ureido)-N-(2-methoxyethyl)-N-methylthiazole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-methoxy-N-methylethanamine (56 μL, 0.625 mmol, 2.5 eq) was added to a DMF (2 mL) solution of 2-(3-(3,4-dichlorobenzyl)ureido)thiazole-4-carboxylic acid (87 mg, 0.25 mmol), TBTU (93 mg, 0.29 mmol, 1.15 eq) and triethylamine (100 μL). After an hour stirring, an aqueous work-up with EtOAc afforded the title compound. 1H NMR (400 MHz, CDCl3): 11.27 (s, 1H), 8.70 (s, 1H), 7.49 (d, 1H), 7.35 (dd, 1H), 7.20 (dd, 1H), 4.40 (d, 2H), 2.80-3.70 (m, 7H, rotamers). MS (ES+): M/Z 417 (M+1).

Sources & evidence

ORD record
ord-d37a23c6deab475090f012d6a583772f
Source dataset
uspto-grants-2014_05
Patent number
US08716320B2

Reaction notes

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