Diisopropylcarbodiimide → HCID 136337187, compound

HRID 1428866Notes

Reaction equation

HRID 1428866 reaction equation
[N:1]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:2]=S.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:17])=[CH:12][CH:11]=1.CC(C)N=C=NC(C)C.[NH:32]1[CH:36]=[C:35]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:34]=[N:33]1>C(Cl)Cl>[CH2:40]([O:39][C:37]([C:35]1[CH:36]=[N:32][N:33]([C:2]([NH:1][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[N:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([N:18]3[CH2:19][CH2:20][CH2:21][CH2:22]3)=[O:17])=[CH:12][CH:11]=2)[CH:34]=1)=[O:38])[CH3:41]

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 85320Ethyl isothiocyanatoformateHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 5778004-(Pyrrolidin-1-ylcarbonyl)aniline

Product 1

HCID 136337187HCID 136337187, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl isothiocyanatoformate (0.60 mL, 5.1 mmol) was added to a suspension of (4-amino-phenyl)-pyrrolidin-1-yl-methanone (0.873 g, 4.59 mmol) in DCM (15 mL) and the reaction mixture was stirred at room temperature for 1 h. DIC (1.01 mL, 5.05 mmol) was then added, followed by ethyl pyrazole-4-carboxylate (0.707 g, 5.05 mmol). Stirring was continued for 18 h, at which point the reaction mixture was concentrated. Diethyl ether (25 mL) was added to the residue and the resulting suspension was cooled to 0° C. and filtered. The filtrate was concentrated and the residue was purified by FCC (2-100% EtOAc/hexanes) to yield the titled compound (1.502 g, 77% yield). MS (ESI/Cl): mass calcd. for C21H25N5O5, 427.2; m/z found, 428.2 [M+H]+.

Workup

  1. stirringStirring
  2. waitwas continued for 18 h, at which
  3. concentrationwas concentrated
  4. additionDiethyl ether (25 mL) was added to the residue
  5. temperaturethe resulting suspension was cooled to 0° C.
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customthe residue was purified by FCC (2-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-4e75532fe9c34d6e888cc124643b389c
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

Loading…