4-Methylmorpholine → N-(4-((3-bromophenyl)amino)-6-quinazolinyl)-2-butynamide

HRID 583093Notes

Reaction equation

HRID 583093 reaction equation
[C:1]([OH:6])(=O)[C:2]#[C:3][CH3:4].ClC(OCC(C)C)=O.CN1CCOCC1.[Br:22][C:23]1[CH:24]=[C:25]([NH:29][C:30]2[C:39]3[C:34](=[CH:35][CH:36]=[C:37]([NH2:40])[CH:38]=3)[N:33]=[CH:32][N:31]=2)[CH:26]=[CH:27][CH:28]=1>O1CCCC1.N1C=CC=CC=1>[Br:22][C:23]1[CH:24]=[C:25]([NH:29][C:30]2[C:39]3[C:34](=[CH:35][CH:36]=[C:37]([NH:40][C:1](=[O:6])[C:2]#[C:3][CH3:4])[CH:38]=3)[N:33]=[CH:32][N:31]=2)[CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 685352-Butynoic acidHCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamine

Product 1

HCID 2776N-(4-((3-bromophenyl)amino)-6-quinazolinyl)-2-butynamideYield 55.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.50 g of 2-butynoic acid in 10 ml of tetrahydrofuran was cooled in an ice bath. A 0.79 ml portion of isobutyl chloroformate followed by a 0.66 ml portion of N-methyl morpholine were added. After about 1 minute a solution of 1.6 g of N-(3-bromophenyl)-4,6-quinazolindiamine in 10 ml of pyridine was added. The reaction was allowed to come to room temperature and stir overnight. The solvents were removed at reduced pressure and the solid was recrystallized from n-butanol to give 1.07 g of N-[4-[(3-bromophenyl)amino]-6-quinazolinyl]-2-butynamide: mass spectrum (m/e): 381,383.

Workup

  1. additionwere added
  2. customto come to room temperature
  3. customThe solvents were removed at reduced pressure
  4. customthe solid was recrystallized from n-butanol

Sources & evidence

ORD record
ord-1aaa26ecf958418893cfcc98f7d49aea
Source dataset
uspto-grants-1999_07
Patent number
US05929080

Reaction notes

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