3-Fluorobenzyl isocyanate → 1-(4-(Chloromethyl)thiazol-2-yl)-1-(2,4-dimethoxybenzyl)-3-(3-fluorobenzyl)urea

HRID 1685025Notes

Reaction equation

HRID 1685025 reaction equation
[Cl:1][CH2:2][C:3]1[N:4]=[C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH3:19])[S:6][CH:7]=1.[F:20][C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=1)[CH2:24][N:25]=[C:26]=[O:27]>C(Cl)Cl>[Cl:1][CH2:2][C:3]1[N:4]=[C:5]([N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH3:19])[C:26]([NH:25][CH2:24][C:23]2[CH:28]=[CH:29][CH:30]=[C:21]([F:20])[CH:22]=2)=[O:27])[S:6][CH:7]=1

Participants

4

Reactant 2

HCID 6434993-Fluorobenzyl isocyanateHCID 866612894-(chloromethyl)-N-(2,4-dimethoxybenzyl)thiazol-2-amine

Product 1

HCID 580550941-(4-(Chloromethyl)thiazol-2-yl)-1-(2,4-dimethoxybenzyl)-3-(3-fluorobenzyl)urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 4-(chloromethyl)-N-(2,4-dimethoxybenzyl)thiazol-2-amine was dissolved in DCM (50 ml) and 3-fluorobenzylisocyanate (1.2 eq.) was added and stirred overnight. The mixture was concentrated and the residue was purified on a column using 0-100% gradient of EtOAc and hexanes to give the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified on a column

Sources & evidence

ORD record
ord-9b435ebd3bb5445783fc6b251a3bdf06
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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