4-Methylmorpholine → HCID 10200067, compound

HRID 1069022Notes

Reaction equation

HRID 1069022 reaction equation
ClC([O:4][CH2:5][CH:6]([CH3:8])C)=O.CN1CC[O:13]CC1.[Br:16][C:17]1[CH:18]=[C:19]([NH:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([NH2:34])[CH:32]=3)[N:27]=[CH:26][N:25]=2)[CH:20]=[CH:21][CH:22]=1.C(OCC)(=O)C>O1CCCC1.O>[Br:16][C:17]1[CH:18]=[C:19]([NH:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([NH:34][C:8]([CH:6]4[CH2:5][O:4]4)=[O:13])[CH:32]=3)[N:27]=[CH:26][N:25]=2)[CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 8857Ethyl AcetateHCID 62365Isobutyl chloroformateHCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamine

Product 1

HCID 10200067HCID 10200067, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 280 mg of 2,3-epoxy propoinic acid in 2.0 mL of tetrahydrofuran was cooled in an ice bath. A 0.42 mL portion of isobutyl chloroformate followed by a 0.48 mL portion of N-methylmorpholine were added. After 5 minutes, a suspension of 500 mg of N-(3-bromophenyl)-4,6-quinazolindiamine in 4 mL of tetrahydrofuran was added. The resulting reaction mixture was stirred at 0° C. for 3 hr., and then was diluted with 30 mL of water. The aqueous solution was extrated with 50 mL of ethyl acetate. The organic phase was separated, dried over Na2SO4 and filtered. The solvent was removed at reduced pressure to give a solid residue. Purification of the crude produt on preparative TLC afforded 109.9 mg of the product as yellow solid in 18 % yield; mp 228-300° C.; mass(m/e) 385.0264.

Workup

  1. additionwere added
  2. additionwas added
  3. customThe resulting reaction mixture
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customThe solvent was removed at reduced pressure
  8. customto give a solid residue
  9. customPurification of the crude produt on preparative TLC

Sources & evidence

ORD record
ord-f697f7ad239a44f1a329b259727718c7
Source dataset
uspto-grants-2001_06
Patent number
US06251912B1

Reaction notes

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