3-Aminopyridine → HCID 22724491, compound

HRID 2231022Notes

Reaction equation

HRID 2231022 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][C:46]1[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=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][C:46]3[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=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:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 100093-AminopyridineHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 22724010HCID 22724010, compound

Product 1

HCID 22724491HCID 22724491, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-benzyl-3-oxo-4-(3-carboxyphenyl)-3,4-dihydropyrido[2,3-b]pyrazine (357 mg), triethylamine (0.14 ml) and diphenylphosphoryl azide (0.216 ml) in benzene (5 ml) was refluxed for 15 minutes. 3-Aminopyridine (113 mg) was then added to the mixture and the reflux was continued for 5 hours. The reaction mixture was poured into a mixture of ethyl acetate and aqueous sodium bicarbonate solution. The organic phase was separated, washed with brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with methanol to give 2-benzyl-3-oxo-4-[3-[3-(3-pyridyl)ureido]phenyl]-3,4-dihydropyrido[2,3-b]pyrazine (168 mg).

Workup

  1. temperaturewas refluxed for 15 minutes
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resultant solid was collected
  7. washwashed with methanol

Sources & evidence

ORD record
ord-3598369f757d49fe8a2953772ae5b939
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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