1,1'-Carbonyldiimidazole → HCID 86629872, compound

HRID 1363734Notes

Reaction equation

HRID 1363734 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH2:5][C:6]1[N:7]=[C:8]([NH2:11])[S:9][CH:10]=1)[CH3:2].[CH:13]1([CH2:18][NH:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[C:22]([F:27])[CH:21]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1.C1N=CN([C:33](N2C=NC=C2)=[O:34])C=1>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH2:1]([O:3][C:4](=[O:12])[CH2:5][C:6]1[N:7]=[C:8]([NH:11][C:33]([N:19]([CH2:18][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17]2)[C:20]2[CH:25]=[CH:24][C:23]([F:26])=[C:22]([F:27])[CH:21]=2)=[O:34])[S:9][CH:10]=1)[CH3:2]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl esterHCID 61344637HCID 61344637, compound

Product 1

HCID 86629872HCID 86629872, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (2-amino-thiazol-4-yl)-acetic acid ethyl ester (1.0 mmol) and cyclopentylmethyl-(3,4-difluoro-phenyl)-amine (1.0 mmol) in dry toluene (10 mL) was added CDI (1.5 mmol) and DMAP (0.05 mmol). The mixture was stirred at 60° C. for 3H an then evaporated to dryness in vacuo. The crude product was purified on silica gel (gradient, from heptane:ethyl acetate (10:1) to heptane:ethyl acetate (3:1)) to give {2-[3-cyclopentylmethyl-3-(3,4-difluoro-phenyl)-ureido]-thiazol-4-yl}-acetic acid ethyl ester.

Workup

  1. customan then evaporated to dryness in vacuo
  2. customThe crude product was purified on silica gel (gradient, from heptane:ethyl acetate (10:1) to heptane:ethyl acetate (3:1))

Sources & evidence

ORD record
ord-f4a4e44b836e4df186763aaf3d440be8
Source dataset
uspto-grants-2011_02
Patent number
US07884210B2

Reaction notes

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