Phenyl isocyanate → HCID 178521957, compound

HRID 2369839Notes

Reaction equation

HRID 2369839 reaction equation
C(N(CC)CC)C.[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:17]1[CH:21]=[C:20]([C:22]2[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=2)[NH:19][N:18]=1.[C:29]1([N:35]=[C:36]=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(#N)C>[NH:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:8]=[C:9]1[C:17]1[CH:21]=[C:20]([C:22]2[CH:28]=[CH:27][C:25]([NH:26][C:36]([NH:35][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:37])=[CH:24][CH:23]=2)[NH:19][N:18]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 178507391HCID 178507391, compound

Product 1

HCID 178521957HCID 178521957, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triethylamine (35 μL, 0.25 mmol) was added to a suspension of 4-[3-(1H-benzimidazol-2-yl)-1H-pyrazol-5-yl]aniline (20 mg, 0.064 mmol) and phenyl isocyanate (7.6 mg, 0.064 mmol) in anhydrous acetonitrile (1.0 mL) at room temperature. After twelve hours the reaction was concentrated in vacuo and purified on reverse phase HPLC using water-acetonitrile gradient (0.1% TFA) to provide the title compound (9 mg, 36% yield) as a white solid: 1H NMR (400 MHz, DMSO-d6): δ 9.08 (s, 1H), 8.92 (s, 1H), 7.78 (m, 4H), 7.63 (m, 2H), 7.48 (m, 4H), 7.40 (s, 1H), 7.30 (m, 2H), 7.00 (m, 1H); MS (EI) for C23H18N6O: 395.2 (MH+).

Workup

  1. concentrationAfter twelve hours the reaction was concentrated in vacuo
  2. custompurified on reverse phase

Sources & evidence

ORD record
ord-bd3860c8b9474406904ed2caaafa7333
Source dataset
uspto-grants-2014_04
Patent number
US08710038B2

Reaction notes

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