alpha-Naphthyl isocyanate → 2-(3-(3-tert-butyl-5-(3-naphthalen-1-ylureido)-1H-pyrazol-1-yl)phenyl)acetamide

HRID 1270509Notes

Reaction equation

HRID 1270509 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([C:11]2[CH:12]=[C:13]([CH2:17][C:18]([NH2:20])=[O:19])[CH:14]=[CH:15][CH:16]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:21]1([N:31]=[C:32]=[O:33])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:32]([NH:31][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=[CH:23][CH:22]=2)=[O:33])[N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][C:18](=[O:19])[NH2:20])[CH:12]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 66589alpha-Naphthyl isocyanateHCID 218673072-(3-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)phenyl)acetamide

Product 1

HCID 218673102-(3-(3-tert-butyl-5-(3-naphthalen-1-ylureido)-1H-pyrazol-1-yl)phenyl)acetamideYield 68.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of Example N (2 g, 0.73 mmol) and 1-naphthylisocyanate (0.124 g, 0.73 mmol) in dry CH2Cl2 (4 ml) was stirred at RT under N2 for 18 h. The solvent was removed in vacuo and the crude product was washed with ethyl acetate (8 ml) and dried in vacuo to yield 1-{3-tert-butyl-1-[3-(carbamoylmethyl)phenyl)-1H-pyrazol-5-yl}-3-(naphthalene-1-yl)urea as a white solid (0.22 g). mp: 230 (dec.); 1H NMR (200 MHz, DMSO-d6): δ 9.12 (s, 1H), 8.92 (s, 1H), 8.32–8.08 (m, 3H), 7.94–7.44 (m, 8H), 6.44 (s, 1H), 3.51 (s, 2H), 1.31 (s, 9H); MS:

Workup

  1. customThe solvent was removed in vacuo
  2. washthe crude product was washed with ethyl acetate (8 ml)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-89e91c92adc949e0b35f7a80938ee04e
Source dataset
uspto-grants-2007_04
Patent number
US07202257B2

Reaction notes

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