Toluene → HCID 22724131, compound

HRID 2086847Notes

Reaction equation

HRID 2086847 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)C1C=CC=CC=1.C([N:30]([CH2:33]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:42])C=CC=CC=1.[NH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][N:54]=1.[C:59]1(C)[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1>O.C(OCC)(=O)C>[CH2:1]([C:8]1[C:13](=[O:14])[N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:30][C:33]([NH:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][N:54]=3)=[O:42])[CH:16]=2)[C:11]2[N:24]=[CH:25][CH:26]=[CH:27][C:10]=2[N:9]=1)[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1

Participants

8

Reactant 5

HCID 1140TolueneHCID 8471TriethylamineHCID 104392-AminopyridineHCID 199401P,P-Diphenylphosphinic azideHCID 22724010HCID 22724010, compound

Product 1

HCID 22724131HCID 22724131, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-benzyl-3-oxo-4-(3-carboxyphenyl)-3,4-dihydropyrido[2,3-b]pyrazine (214 mg), triethylamine (0.084 ml) and diphenylphosphoryl azide (0.129 ml) in toluene (4 ml) was refluxed for 30 minutes. 2-Aminopyridine (113 mg) was then added to the mixture and reflux was continued for 1 hour. The reaction mixture was poured into a mixture of ethyl acetate and water. The organic phase was separated, washed with brine, dried over magnesium sulfate, concentrated and subjected to silica gel column chromatography (hexane-ethyl acetate, 1:3) to afford 2-benzyl-3-oxo-4-[3-[3-(2-pyridyl)ureido]phenyl]-3,4-dihydropyrido[2,3-b]pyrazine (48 mg) as a solid.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. temperaturereflux
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c339cc447a644b458e374075a4aa5f02
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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