4-Methylmorpholine → HCID 15550657, compound

HRID 1266259Notes

Reaction equation

HRID 1266259 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]#[N:13])=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[CH:16]=1.CN1CCOCC1.[C:29](Cl)(=[O:32])[CH:30]=[CH2:31]>CN(C)C=O.O1CCCC1>[Br:21][C:17]1[CH:16]=[C:15]([NH:14][C:5]2[C:6]([C:12]#[N:13])=[CH:7][N:8]=[C:9]3[C:4]=2[CH:3]=[C:2]([NH:1][C:29](=[O:32])[CH:30]=[CH2:31])[CH:11]=[N:10]3)[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 13140Acryloyl chlorideHCID 99498136-Amino-4-(3-bromo-phenylamino)-[1,8]naphthyridine-3-carbonitrile

Product 1

HCID 15550657HCID 15550657, compoundYield 17.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.4 g (4.12 mmol) of 6-amino-4-(3-bromo-phenylamino)-[1.8]naphthyridine-3-carbonitrile and 1.67 g (16.5 mmol) of N-methyl-morpholine in a mixture of 6 ml of N,N-dimethylformamide and 35 ml of tetrahydrofuran was added with stirring at 0° C. a solution of 0.52 g (5.76 mmol) of acryloyl chloride in 10 ml of tetrahydrofuran over 10 min. After 3 hr at 0° C., the most of the solvent was removed saturated sodium bicarbonate was added. Solid was collected and washed with water. After air drying, the solid was extracted with 500 ml of boiling tetrahydrofuran. The tetrahydrofuran was removed and the residue was purified on a silica gel column eluting with ethyl acetate-methanol mixtures giving 0.29 g of the title compound as a yellow solid: mass spectrum (electrospray, m/e): M+H 394, 396.

Workup

  1. additionwas added
  2. customthe most of the solvent was removed saturated sodium bicarbonate
  3. additionwas added
  4. customSolid was collected
  5. washwashed with water
  6. customAfter air drying
  7. extractionthe solid was extracted with 500 ml of boiling tetrahydrofuran
  8. customThe tetrahydrofuran was removed
  9. customthe residue was purified on a silica gel column
  10. washeluting with ethyl acetate-methanol

Sources & evidence

ORD record
ord-bff929e5db1043cfa0d24b7bb73ad230
Source dataset
uspto-grants-2003_04
Patent number
US06548496B2

Reaction notes

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