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

HRID 570064Notes

Reaction equation

HRID 570064 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 one-fourth 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-2125172c98c5459c9bed204310ad8ca5
Source dataset
uspto-grants-1988_03
Patent number
US04734510

Reaction notes

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