Triphenylphosphine → HCID 178508341, compound

HRID 646731Notes

Reaction equation

HRID 646731 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH2:20][C:21]1[N:22]=[CH:23][C:24]([C:38]2[CH:39]=[C:40]([CH2:44]O)[CH:41]=[CH:42][CH:43]=2)=[N:25][C:26]=1[C:27]1[NH:31][C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[N:29][N:28]=1.[C@@H:46]1([NH:55][S:56]([C:59]2[CH:64]=[CH:63][C:62]([N+:65]([O-:67])=[O:66])=[CH:61][C:60]=2[N+:68]([O-:70])=[O:69])(=[O:58])=[O:57])[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH2:48][CH2:47]1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C(OCC)(=O)C>[NH2:20][C:21]1[N:22]=[CH:23][C:24]([C:38]2[CH:39]=[C:40]([CH:41]=[CH:42][CH:43]=2)[CH2:44][N:55]([C@@H:46]2[C:54]3[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=3)[CH2:48][CH2:47]2)[S:56]([C:59]2[CH:64]=[CH:63][C:62]([N+:65]([O-:67])=[O:66])=[CH:61][C:60]=2[N+:68]([O-:70])=[O:69])(=[O:58])=[O:57])=[N:25][C:26]=1[C:27]1[NH:31][C:30]([CH2:32][C:33]2[CH:1]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:29][N:28]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86607845N-[(1S)-2,3-dihydro-1H-inden-1-yl]-2,4-dinitrobenzen sulfonamideHCID 178508343HCID 178508343, compound

Product 1

HCID 178508341HCID 178508341, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triphenylphosphine (47 mg, 0.17 mmol) was added to a stirred solution of {3-[5-amino-6-(5-phenyl-4H-1,2,4-triazol-3-yl) pyrazine-2-yl]phenyl}methanol (50 mg, 0.14 mmol) and N-[(1S)-2,3-dihydro-1H-inden-1-yl]-2,4-dinitrobenzen sulfonamide (60 mg, 0.16 mmol) in THF. Diethyl azodicarboxylate (31 mg, 0.17 mmol) was then added and mixture was stirred at ambient temperature 4 h. Ethyl acetate (20 mL) was added, and the organic layer was washed with saturated aqueous sodium chloride, and then dried (Na2SO4). Filtration and concentration followed by chromatography on silica gel afforded the title compound: MS (EI) for C35H29N9O6S: 704 (MH+).

Workup

  1. washthe organic layer was washed with saturated aqueous sodium chloride
  2. dry with materialdried (Na2SO4)
  3. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-0dfe80fcffe04a9cacdd4cee45d0e875
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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