1,1'-Carbonyldiimidazole → HCID 86639125, compound

HRID 1881120Notes

Reaction equation

HRID 1881120 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][S:5][C:6]1[S:10][C:9]([NH2:11])=[N:8][CH:7]=1.C1N=CN([C:18](N2C=NC=C2)=[O:19])C=1.[F:25][C:26]([F:42])([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:27][NH:28][CH:29]1[CH2:34][CH2:33][CH:32]([CH3:35])[CH2:31][CH2:30]1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3](=[O:12])[CH2:4][S:5][C:6]1[S:10][C:9]([NH:11][C:18]([N:28]([CH2:27][C:26]([F:42])([F:25])[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:29]2[CH2:30][CH2:31][CH:32]([CH3:35])[CH2:33][CH2:34]2)=[O:19])=[N:8][CH:7]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 24704801Methyl 2-[(2-amino-5-thiazolyl)thio]acetateHCID 57431483HCID 57431483, compound

Product 1

HCID 86639125HCID 86639125, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of (2-amino-thiazol-5-ylsulfanyl)-acetic acid methyl ester (403 mg, 1.98 mmol) in CH2Cl2 (100 mL) was added CDI (480.2 mg, 2.96 mmol) and DMAP (25 mg, 0.20 mmol) at room temperature. The reaction mixture was stirred at room temperature for 1.5 h, and then (2,2-difluoro-2-phenyl-ethyl)-(4-methyl-cyclohexyl)-amine (500 mg, 1.98 mmol) was added. The mixture was stirred for 16 h at room temperature. The solvent was removed at reduced pressure and the residue was purified by preparative HPLC to give {2-[3-(2,2-difluoro-2-phenyl-ethyl)-3-(4-methyl-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid methyl ester.

Workup

  1. stirringThe mixture was stirred for 16 h at room temperature
  2. customThe solvent was removed at reduced pressure
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-4f07bcc89c90467e87acd2d9b71644fc
Source dataset
uspto-grants-2012_11
Patent number
US08318778B2

Reaction notes

Loading…