Water → HCID 70571687, compound

HRID 2403600Notes

Reaction equation

HRID 2403600 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][N:15]([CH3:27])[C:16](=[O:26])[CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:9]=2)=[CH:4][CH:3]=1.[CH3:28][CH:29]([N:31]=[C:32]=[O:33])[CH3:30].O>ClCCl>[CH:29]([NH:31][C:32]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][N:15]([CH3:27])[C:16](=[O:26])[CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:24])[CH3:22])[CH:9]=2)=[CH:4][CH:3]=1)=[O:33])([CH3:30])[CH3:28]

Participants

5

Reactant 3

HCID 962WaterHCID 61277Isopropyl isocyanateHCID 70570127HCID 70570127, compound

Product 1

HCID 70571687HCID 70571687, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of tert-butyl (2-{[(4′-aminobiphenyl-3-yl)methyl](methyl)amino]-2-oxoethyl}carbamate (200 mg) in dichloromethane (4 ml) was added 2-propyl isocyanate (55 mg), followed by stirring at room temperature for 2 hours. To the reaction mixture was added water, followed by stirring, and the organic layer was purified by silica gel column chromatography (2% MeOH/CHCl3) to obtain tert-butyl {2-[({4′-[(isopropylcarbamoyl)amino]biphenyl-3-yl}methyl)(methyl)amino]-2-oxoethyl}carbamate (240 mg) as a colorless oil.

Workup

  1. stirringby stirring
  2. customthe organic layer was purified by silica gel column chromatography (2% MeOH/CHCl3)

Sources & evidence

ORD record
ord-9e0341d9991c4b09aa765f4beb125ea8
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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