4-Chloro-6,7-dimethoxyquinazoline → HCID 68193772, compound

HRID 536073Notes

Reaction equation

HRID 536073 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[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:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][N:3]=[C:2]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]

Participants

4

Reactant 2

HCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 43382810HCID 43382810, compound

Product 1

HCID 68193772HCID 68193772, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-6,7-bis(methyloxy)quinazoline (100 mg, 0.445 mmol) and 3-amino-N-methyl-4-[(2,2,2-trifluoroethyl)oxy]benzenesulfonamide (139 mg, 0.490 mmol) in i-PrOH (2 mL) was subjected to microwave irradiation (100° C., 2 bar) for 30 minutes before being cooled to room temperature. The solid that formed was collected by filtration and washed with isopropanol to give 3-{[6,7-bis(methyloxy)-4-quinazolinyl]amino}-N-methyl-4-[(2,2,2-trifluoroethyl)oxy]benzenesulfonamide hydrochloride (160 mg, 70%) as a pale yellow solid.

Workup

  1. customwas subjected to microwave irradiation (100° C., 2 bar) for 30 minutes
  2. customThe solid that formed
  3. filtrationwas collected by filtration
  4. washwashed with isopropanol

Sources & evidence

ORD record
ord-71d2bd9e14404d728bcef4c19dcbbca8
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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