Triethylamine → HCID 178521862, compound

HRID 2369833Notes

Reaction equation

HRID 2369833 reaction equation
C([N:3]([CH2:6][CH3:7])CC)C.[C:8]1([C:14]2[CH:18]=[C:17](NC3C=CC=CC=3)[NH:16][N:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[O:35])=[CH:29][C:28]=1[C:36]([F:39])([F:38])[F:37]>C(#N)C>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34]([NH:3][C:6]2[CH:7]=[CH:10][C:9]([C:17]3[CH:18]=[C:14]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)[NH:15][N:16]=3)=[CH:8][CH:13]=2)=[O:35])=[CH:29][C:28]=1[C:36]([F:37])([F:38])[F:39]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 178420467HCID 178420467, compound

Product 1

HCID 178521862HCID 178521862, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triethylamine (64 mL, 0.45 mmol) was added to a suspension of N-[4-(3-phenyl-1H-pyrazol-5-yl)aminobenzene (0.102 g, 0.43 mmol) and 4-chloro-3-trifluoromethyl-phenylisocyanate (0.096 g, 0.43 mmol) in anhydrous acetonitrile (2.0 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 (23 mg, 16% yield) as a white solid: 1H NMR (400 MHz, DMSO-d6): δ 9.24 (s, 1H), 9.01 (s, 1H), 8.11 (d, J=2.0 Hz, 1H), 7.81 (m, 2H), 7.74 (m, 2H), 7.62 (m, 2H), 7.53 (m, 2H), 7.42 (t, J=8.0 Hz, 2H), 7.32 (t, J=7.6 Hz, 1H), 7.10 (s, 1H); MS (EI) for C23H16ClF3N4O: 457.1 (MH+).

Workup

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

Sources & evidence

ORD record
ord-e229941e12ae4aad942350723b17df3a
Source dataset
uspto-grants-2014_04
Patent number
US08710038B2

Reaction notes

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