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

HRID 235661
Notes
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Reaction equation

HRID 235661 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6212
Chloroform
Solvent

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 sitrring. 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-e25c26d4d6ff481d8a27bb56cd15ecc4
Source dataset
uspto-grants-1987_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04640920

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes