Tetrahydrofuran → {2-Amino-6-[2-(2,5-dimethylpyrrolidine-1-sulfonyl)phenyl]-quinazolin-4-yl}-(1,3-dihydroisoindol-2-yl)methanone

HRID 1037686Notes

Reaction equation

HRID 1037686 reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][N:3]1C.[NH2:8][C:9]1[N:18]=[C:17]([C:19]([N:21]2[CH2:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22]2)=[O:20])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[S:36](Cl)(=[O:38])=[O:37])[CH:15]=2)[N:10]=1.[CH2:40]1COCC1>>[NH2:8][C:9]1[N:18]=[C:17]([C:19]([N:21]2[CH2:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22]2)=[O:20])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[S:36]([N:3]3[CH:4]([CH3:40])[CH2:5][CH2:6][CH:2]3[CH3:1])(=[O:38])=[O:37])[CH:15]=2)[N:10]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 102483Pyrrolidine, 1,2-dimethyl-HCID 584571942-[2-Amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]benzenesulfonyl chloride

Product 1

HCID 46701565{2-Amino-6-[2-(2,5-dimethylpyrrolidine-1-sulfonyl)phenyl]-quinazolin-4-yl}-(1,3-dihydroisoindol-2-yl)methanone

Conditions

Temperature
22 °C

Procedure

A solution of 58 μl of dimethylpyrrolidine in 4 ml of THF is added dropwise to a solution of 400 mg of 2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)-quinazolin-6-yl]benzenesulfonyl chloride in 4 ml of THF with ice-cooling. The mixture is subsequently stirred at 22° C. for a further 1 h, evaporated in vacuo and taken up in 4 ml of diethyl ether. The solution is washed 3 times against sodium hydroxide solution (2N) and finally purified by column chromatography.

Workup

  1. temperaturecooling
  2. customevaporated in vacuo
  3. washThe solution is washed 3 times against sodium hydroxide solution (2N)
  4. customfinally purified by column chromatography

Sources & evidence

ORD record
ord-4e44cb001b3347f1b931d08d32a30a4e
Source dataset
uspto-grants-2013_10
Patent number
US08546565B2

Reaction notes

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