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

HRID 430494Notes

Reaction equation

HRID 430494 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-be17a86decdd4ca89b9aee296451dc21
Source dataset
uspto-grants-2001_11
Patent number
US06323209B1

Reaction notes

Loading…