4-Chloro-5,7-dimethoxyquinazoline → HCID 68194054, compound

HRID 536074Notes

Reaction equation

HRID 536074 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[CH:9][C:10]=2[O:12][CH3:13])[N:5]=[CH:4][N:3]=1.[NH2:16][C:17]1[CH:18]=[C:19]([S:29]([NH:32][CH3:33])(=[O:31])=[O:30])[CH:20]=[CH:21][C:22]=1[O:23][CH2:24][C:25]([F:28])([F:27])[F:26]>CC(O)C>[ClH:1].[CH3:13][O:12][C:10]1[CH:9]=[C:8]([O:14][CH3:15])[CH:7]=[C:6]2[C:11]=1[C:2]([NH:16][C:17]1[CH:18]=[C:19]([S:29]([NH:32][CH3:33])(=[O:30])=[O:31])[CH:20]=[CH:21][C:22]=1[O:23][CH2:24][C:25]([F:27])([F:26])[F:28])=[N:3][CH:4]=[N:5]2

Participants

4

Reactant 2

HCID 221407334-Chloro-5,7-dimethoxyquinazolineHCID 43382810HCID 43382810, compound

Product 1

HCID 68194054HCID 68194054, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-5,7-bis(methyloxy)quinazoline (75 mg, 0.334 mmol, prepared according to J. Med. Chem. (2006) 49 6465) and 3-amino-N-methyl-4-[(2,2,2-trifluoroethyl)oxy]benzenesulfonamide (95 mg, 0.334 mmol) in i-PrOH (2 mL) was subjected to microwave irradiation (100° C., 1 bar) for 30 minutes before being cooled to room temperature. The solid was collected by filtration, washed with i-PrOH, and dried under vacuum to give 3-{[5,7-bis(methyloxy)-4-quinazolinyl]amino}-N-methyl-4-[(2,2,2-trifluoroethyl)oxy]benzenesulfonamide hydrochloride (130 mg, 76%) as a yellow soid.

Workup

  1. customwas subjected to microwave irradiation (100° C., 1 bar) for 30 minutes
  2. filtrationThe solid was collected by filtration
  3. washwashed with i-PrOH
  4. customdried under vacuum

Sources & evidence

ORD record
ord-29d661d61c2e44df92752fb56ff1cf8c
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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