4-Methylmorpholine → HCID 9887722, compound

HRID 430497Notes

Reaction equation

HRID 430497 reaction equation
[CH:1]1([C:6]([OH:8])=O)[CH2:5][CH2:4][CH:3]=[CH:2]1.ClC(OCC(C)C)=O.CN1CCOCC1.[Br:24][C:25]1[CH:26]=[C:27]([NH:31][C:32]2[C:41]3[C:36](=[CH:37][CH:38]=[C:39]([NH2:42])[CH:40]=3)[N:35]=[CH:34][N:33]=2)[CH:28]=[CH:29][CH:30]=1>O1CCCC1.N1C=CC=CC=1>[Br:24][C:25]1[CH:26]=[C:27]([NH:31][C:32]2[C:41]3[C:36](=[CH:37][CH:38]=[C:39]([NH:42][C:6]([CH:1]4[CH2:5][CH2:4][CH:3]=[CH:2]4)=[O:8])[CH:40]=3)[N:35]=[CH:34][N:33]=2)[CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 5491712-Cyclopentene-1-carboxylic acidHCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamine

Product 1

HCID 9887722HCID 9887722, compoundYield 23.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.43 g of 2-cyclopentenoic acid in 5 ml of tetrahydrofuran was cooled in an ice bath. A 0.49 ml portion of isobutyl chloroformate followed by a 0.41 ml portion of N-methyl morpholine were added. After about 1 minute a solution of 1.0 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. Another 0.5 equivalents of mixed anhydride was added. The mixture was stirred for 5 hours. The solvents were removed at reduced pressure and the solid was purified by chromatography on silica gel to give 0.30 g of N-[4-[(3-bromophenyl)amino]-6-quinazolinyl]-2-cyclopenteneamide: mass spectrum (m/e): 409 (M+H, EI).

Workup

  1. additionwere added
  2. customto come to room temperature
  3. stirringThe mixture was stirred for 5 hours
  4. customThe solvents were removed at reduced pressure
  5. customthe solid was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a9e4ab00a898433dab1f6aa35b58f243
Source dataset
uspto-grants-2001_11
Patent number
US06323209B1

Reaction notes

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