Water → HCID 52932691, compound

HRID 536077Notes

Reaction equation

HRID 536077 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[CH:14]=[C:15]([S:25]([NH:28][CH3:29])(=[O:27])=[O:26])[CH:16]=[CH:17][C:18]=3[O:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:30][CH3:31].Br[CH:33]([CH3:35])[CH3:34].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH:33]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[CH:14]=[C:15]([S:25]([NH:28][CH3:29])(=[O:26])=[O:27])[CH:16]=[CH:17][C:18]=3[O:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:30][CH3:31])([CH3:35])[CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 135980476HCID 135980476, compound

Product 1

HCID 52932691HCID 52932691, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3-{[7-hydroxy-6-(methyloxy)-4-quinazolinyl]amino}-N-methyl-4-[(2,2,2-trifluoroethyl)oxy]benzenesulfonamide (170 mg, 0.37 mmol) in DMF (5 mL) was treated with 2-bromopropane (181 mg, 1.48 mmol) and K2CO3 (154 mg, 1.11 mmol) and stirred at 60° C. for 16 hours before being poured into water. The precipitate that formed was collected by filtration, washed with MeOH, and dried to give 3-(7-isopropoxy-6-methoxy-quinazolin-4-ylamino)-N-methyl-4-(2,2,2-trifluoro-ethoxy)-benzenesulfonamide (80 mg, 43%) as an off-white solid.

Workup

  1. customThe precipitate that formed
  2. filtrationwas collected by filtration
  3. washwashed with MeOH
  4. customdried

Sources & evidence

ORD record
ord-ac2765c8422d4324b9d15fd8eec9f9d1
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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