4-Toluenesulfonyl chloride → HCID 86610962, compound

HRID 2354207Notes

Reaction equation

HRID 2354207 reaction equation
[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH2:25][C:26]([OH:30])([CH3:29])[CH2:27][OH:28])[CH:20]=4)[N:15]=[CH:14]3)[CH:7]=2)[CH2:3][CH2:2]1.[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH3:42][C:32]1[CH:37]=[CH:36][C:35]([S:38]([O:28][CH2:27][C:26]([OH:30])([CH3:29])[CH2:25][O:24][C:19]2[CH:20]=[C:21]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][N:13]([C:8]2[CH:7]=[C:6]([C:5]([NH:4][CH:1]4[CH2:3][CH2:2]4)=[O:31])[CH:11]=[CH:10][C:9]=2[CH3:12])[C:22]3=[O:23])(=[O:40])=[O:39])=[CH:34][CH:33]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 11774562N-cyclopropyl-3-[6-(2,3-dihydroxy-2-methylpropoxy)-4-oxoquinazolin-3(4H)-yl]-4-methylbenzamide

Product 1

HCID 86610962HCID 86610962, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-cyclopropyl-3-[6-(2,3-dihydroxy-2-methylpropoxy)-4-oxoquinazolin-3(4H)-yl]-4-methylbenzamide (0.2 g) in pyridine (10 ml) was added p-toluenesulfonylchloride (0.18 g) followed by 4-dimethylaminopyridine (cat.) and the mixture heated at 60° C. for 18 hours. The reaction mixture was concentrated under reduced pressure and redissolved in ethyl acetate. The organics were washed with 1N citric acid, brine, dried (magnesium sulfate) and concentrated to give the crude 3-[(3-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-4-oxo-3,4-dihydroquinazolin-6-yl)oxy]-2-hydroxy-2-methylpropyl 4-methylbenzenesulfonate (0.21 g) which was used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionredissolved in ethyl acetate
  3. washThe organics were washed with 1N citric acid, brine
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b3cd834edd944ce78a74e186847e1096
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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