Sodium Carbonate → N-[(1-ethyl-2-pyrrolidinyl)methyl]-4-(7-trifluoromethyl-4-quinazolinylamino)benzamide

HRID 1383077Notes

Reaction equation

HRID 1383077 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][CH3:9].[C:10](=[O:13])([O-])[O-].[Na+].[Na+].Cl.[F:17][C:18]([F:41])([F:40])[C:19]1[CH:28]=[C:27]2[C:22]([C:23]([NH:29][C:30]3[CH:35]=[CH:34][C:33](S(Cl)(=O)=O)=[CH:32][CH:31]=3)=[N:24][CH:25]=[N:26]2)=[CH:21][CH:20]=1>C(Cl)(Cl)Cl>[CH2:8]([N:4]1[CH2:5][CH2:6][CH2:7][CH:3]1[CH2:2][NH:1][C:10](=[O:13])[C:33]1[CH:32]=[CH:31][C:30]([NH:29][C:23]2[C:22]3[C:27](=[CH:28][C:19]([C:18]([F:40])([F:41])[F:17])=[CH:20][CH:21]=3)[N:26]=[CH:25][N:24]=2)=[CH:35][CH:34]=1)[CH3:9]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 867412594-(7-Trifluoromethyl-4-quinazolinylamino)benzene sulphonylchloride hydrochloride

Product 1

HCID 21273959N-[(1-ethyl-2-pyrrolidinyl)methyl]-4-(7-trifluoromethyl-4-quinazolinylamino)benzamideYield 26.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2-aminomethyl-1-ethylpyrrolidine (0.34 ml; 0.00235 mole), anhydrous sodium carbonate (3.5 g) and chloroform (100 ml) was cooled on an ice bath and treated with 4-(7-trifluoromethyl-4-quinazolinylamino)benzene sulphonylchloride hydrochloride (1.0 g; 0.00235 mole) with vigorous stirring. The mixture was stirred at ambient temperature for 4 hours and then filtered. The residue on evaporation of the solvent was triturated with ether and the resulting solid was filtered off, washed with a little ether and dried to give the quarter hydrate of the title compound (0.28 g), melting point 150°-152° C.

Workup

  1. temperaturewas cooled on an ice bath
  2. filtrationfiltered
  3. customThe residue on evaporation of the solvent
  4. customwas triturated with ether
  5. filtrationthe resulting solid was filtered off
  6. washwashed with a little ether
  7. customdried

Sources & evidence

ORD record
ord-313c31bbbfcd410e96cc442e79e96a2c
Source dataset
uspto-grants-1989_02
Patent number
US04808715

Reaction notes

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