Ethyl isocyanate → HCID 67499248, compound

HRID 1428354Notes

Reaction equation

HRID 1428354 reaction equation
[CH3:1][C:2]1[C:6]([NH2:7])=[CH:5][N:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[N:3]=1.[CH2:14]([N:16]=[C:17]=[O:18])[CH3:15]>C(Cl)Cl>[CH2:14]([NH:16][C:17]([NH:7][C:6]1[C:2]([CH3:1])=[N:3][N:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=1)=[O:18])[CH3:15]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 67498744HCID 67498744, compound

Product 1

HCID 67499248HCID 67499248, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine (0.1 g, 0.574 mmol) in DCM (5.74 ml) was added ethyl isocyanate (0.041 g, 0.574 mmol) and the reaction mixture was stirred at ambient temperature for 40 minutes. The reaction mixture had turned from a clear solution to a suspension with white solid material. The reaction mixture was concentrated and purified using silica gel chromatography (0-20% MeOH/DCM) to yield the title compound as a white solid (0.135 g, 95%): mp 197-200° C.; 1H NMR (400 MHz, CDCl3) δ 8.94 (d, J=2.3 Hz, 1H), 8.48-8.37 (m, 1H), 8.32 (s, 1H), 7.94 (d, J=8.3 Hz, 1H), 7.52 (br s, 1H), 7.41-7.25 (m, 1H), 5.79 (br s, 1H), 3.33-3.23 (m, 2H), 2.29 (d, J=2.9 Hz, 3H), 1.16 (dd, J=8.7, 5.7 Hz, 3H); ESIMS m/z 246 ([M+H]+), 244 ([M−H]−).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified

Sources & evidence

ORD record
ord-8b102fe06b1f47088ff2824d04792fb1
Source dataset
uspto-grants-2015_01
Patent number
US08937083B2

Reaction notes

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