Diisopropylcarbodiimide → HCID 178473531, compound

HRID 1428821Notes

Reaction equation

HRID 1428821 reaction equation
[CH3:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:3]=1[O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][C:6]=1[CH3:12].[N:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:19]=S.[NH:26]1[CH:30]=[C:29]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:28]=[N:27]1.CC(C)N=C=NC(C)C>C(Cl)Cl>[CH2:34]([O:33][C:31]([C:29]1[CH:30]=[N:26][N:27]([C:19]([NH:9][C:8]2[CH:10]=[CH:11][C:5]([O:4][C:3]3[C:2]([CH3:1])=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:17])=[C:6]([CH3:12])[CH:7]=2)=[N:18][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:28]=1)=[O:32])[CH3:35]

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 85320Ethyl isothiocyanatoformateHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 43165626HCID 43165626, compound

Product 1

HCID 178473531HCID 178473531, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(2,6-dimethyl-phenoxy)-3-methyl-aniline (0.80 g, 3.5 mmol), ethyl isothiocyanatoformate (0.40 mL, 3.5 mmol) and DCM (30 mL) was stirred at room temperature for 1 h. Ethyl pyrazole-4-carboxylate (0.54 g, 3.9 mmol) and DIC (0.54 mL, 3.5 mmol) were added, and the solution was stirred at room temperature for 16 h. The mixture was concentrated and purified by FCC (EtOAc/hexanes 0:100 to 50:50) to provide the titled compound (0.97 g, 60%). MS (ESI): mass calcd. for C25H28N4O5, 464.5; m/z found, 465.1 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by FCC (EtOAc/hexanes 0:100 to 50:50)

Sources & evidence

ORD record
ord-bb6351fdb49e436cac922886fd40c22c
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

Loading…