N-Aminomorpholine → HCID 22724216, compound

HRID 2231043Notes

Reaction equation

HRID 2231043 reaction equation
[CH2:1]([C:8]1[C:13](=[O:14])[N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17](C(O)=O)[CH:16]=2)[C:11]2[N:24]=[CH:25][CH:26]=[CH:27][C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P([N:42]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[NH2:45][N:46]1[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1.[C:52](=[O:55])(O)[O-].[Na+]>C1C=CC=CC=1.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:1]([C:8]1[C:13](=[O:14])[N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:42][C:52]([NH:45][N:46]3[CH2:51][CH2:50][O:49][CH2:48][CH2:47]3)=[O:55])[CH:16]=2)[C:11]2[N:24]=[CH:25][CH:26]=[CH:27][C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 20315N-AminomorpholineHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 22724010HCID 22724010, compound

Product 1

HCID 22724216HCID 22724216, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-benzyl-4-(3-carboxyphenyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (339 mg), diphenylphosphoryl azide (0.21 ml) and triethylamine (0.14 ml) in benzene (5 ml) was stirred under reflux for 30 minutes. Then 4-aminomorpholine (0.11 ml) was added to the mixture and reflux was continued additional 3 hours. The mixture was poured into a mixture of ethyl acetate and aqueous sodium bicarbonate. The organic phase was separated, washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column (3% methanol in chloroform) to give 2-benzyl-4-[3-(3-morpholinoureido)phenyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (138 mg).

Workup

  1. temperatureunder reflux for 30 minutes
  2. temperaturereflux
  3. customThe organic phase was separated
  4. washwashed with aqueous sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel column (3% methanol in chloroform)

Sources & evidence

ORD record
ord-2678e8d288c64fd7aca5ebb2ce57ce15
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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