Methyl Isocyanate → HCID 11374576, compound

HRID 1879949Notes

Reaction equation

HRID 1879949 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[Cl:5][C:6]1[C:7]([F:32])=[C:8]([CH:29]=[CH:30][CH:31]=1)[NH:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:27][CH3:28])=[C:17]([O:20][CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[CH:18]=2)[N:13]=[CH:12][N:11]=1>ClCCl>[Cl:5][C:6]1[C:7]([F:32])=[C:8]([CH:29]=[CH:30][CH:31]=1)[NH:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:27][CH3:28])=[C:17]([O:20][CH:21]3[CH2:26][CH2:25][N:24]([C:3](=[O:4])[NH:2][CH3:1])[CH2:23][CH2:22]3)[CH:18]=2)[N:13]=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 10408840N-(3-chloro-2-fluorophenyl)-7-methoxy-6-(piperidin-4-yloxy)quinazolin-4-amine

Product 1

HCID 11374576HCID 11374576, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methylisocyanate (20.4 μl, 0.33 mmol) was added dropwise to a mixture of 4-(3-chloro-2-fluoroanilino)-7-methoxy-6-[(piperidin-4-yl)oxy]quinazoline (120 mg, 0.3 mmol) in dichloromethane (5 ml) at room temperature. The mixture was stirred at room temperature for 4 hours. After evaporation of the solvents under vacuum, the residue was purified by chromatography on silica gel (eluant: 2% 7N methanolic ammonia in dichloromethane) to give the title compound as a white solid (100 mg, 72%).

Workup

  1. customAfter evaporation of the solvents under vacuum
  2. customthe residue was purified by chromatography on silica gel (eluant: 2% 7N methanolic ammonia in dichloromethane)

Sources & evidence

ORD record
ord-c9c6a8dad6e5477e8f38034784ff838b
Source dataset
uspto-grants-2012_11
Patent number
US08318752B2

Reaction notes

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