Water → N-[4-(6-Chloro-2,3-dihydro-indol-1-yl)-quinazolin-7-yl]methanesulfonamide

HRID 1597988Notes

Reaction equation

HRID 1597988 reaction equation
Cl.[Cl:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][N:9]2[C:12]2[C:21]3[C:16](=[CH:17][C:18]([NH2:22])=[CH:19][CH:20]=3)[N:15]=[CH:14][N:13]=2)=[CH:5][CH:4]=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25].C(N(CC)CC)C.O>C(Cl)(Cl)Cl>[Cl:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][N:9]2[C:12]2[C:21]3[C:16](=[CH:17][C:18]([NH:22][S:24]([CH3:23])(=[O:26])=[O:25])=[CH:19][CH:20]=3)[N:15]=[CH:14][N:13]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 189328104-(6-Chloro-2,3-dihydro-indol-1-yl)-quinazolin-7-yl amine hydrochloride

Product 1

HCID 18932797N-[4-(6-Chloro-2,3-dihydro-indol-1-yl)-quinazolin-7-yl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-(6-Chloro-2,3-dihydro-indol-1-yl)-quinazolin-7-yl amine hydrochloride (0.155 g, 0.465 mmol) was reacted with methanesulfonyl chloride (0.0531, 0.465 mmol) and triethylamine (0.290 g, 2.87 mmol) in 5 mL of chloroform at 0° C. for one hour and 16 hours at room temperature. The reaction mixture was poured into 50 mL of water and extracted with 3×50 mL of ethyl acetate. The pooled organic layers were washed with 50 mL of brine, dried with magnesium sulfate, filtered and vacuum evaporated to a yellow residue, 0.121 g. This was purified by chromatography using a Chromatotron mounted with a 2 mm silica gel plate and eluted with 5% methanol in chloroform. Pure product was isolated by vacuum evaporation of the appropriate fractions; 0.015 g (8.7%) M.P. 240°-245° C. (dec).

Workup

  1. extractionextracted with 3×50 mL of ethyl acetate
  2. washThe pooled organic layers were washed with 50 mL of brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. customvacuum evaporated to a yellow residue, 0.121 g
  6. customThis was purified by chromatography
  7. washeluted with 5% methanol in chloroform
  8. customPure product was isolated by vacuum evaporation of the appropriate fractions

Sources & evidence

ORD record
ord-aeaa38cd5b224cbab2b25d80d1ae07cf
Source dataset
uspto-grants-1998_04
Patent number
US05736534

Reaction notes

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