Piperidine → HCID 178517294, compound

HRID 1615229Notes

Reaction equation

HRID 1615229 reaction equation
[F:1][C:2]([F:15])([F:14])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2.[NH:16]1[C:20]2[CH:21]=[CH:22][C:23]([CH:25]=O)=[CH:24][C:19]=2[N:18]=[N:17]1.N1CCCCC1>CO>[NH:16]1[C:20]2[CH:21]=[CH:22][C:23](/[CH:25]=[C:7]3/[C:8](=[O:13])[NH:9][C:10]4[C:6]/3=[CH:5][C:4]([O:3][C:2]([F:1])([F:14])[F:15])=[CH:12][CH:11]=4)=[CH:24][C:19]=2[N:18]=[N:17]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 253071632-Oxo-5-(trifluoromethoxy)indolineHCID 178519382HCID 178519382, compound

Product 1

HCID 178517294HCID 178517294, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A scintillation vial was charged with 5-(trifluoromethoxy)indolin-2-one (27 mg, 0.124 mmol), 1H-benzo[d][1,2,3]triazole-5-carbaldehyde (20 mg, 0.136 mmol), piperidine (2 uL, 0.012 mmol) and MeOH (2 mL). The reaction was then heated to 60° C. for 2 hrs. The MeOH was removed in vacuo and the residue purified by column chromatography (silica gel, 95:4:1, CH2Cl2/MeOH/AcOH) to give the title compound as a yellow solid (10 mg, 23%). 1H NMR (400 MHz, CD3OD) δ 8.23 (s, 1H), 8.04 (d, J=4.5 Hz, 1H), 8.02 (s, 1H), 7.77 (d, J=9.3 Hz, 1H), 7.42 (s, 1H), 7.21-7.18 (m, 1H), 6.99 (s, 1H); MS ESI 347.0 [M+H]+, calcd for [C16H9F3N4O2+H]+ 347.08.

Workup

  1. customThe MeOH was removed in vacuo
  2. customthe residue purified by column chromatography (silica gel, 95:4:1, CH2Cl2/MeOH/AcOH)

Sources & evidence

ORD record
ord-e7e4e1b079f14f6e90ea30dae31c4467
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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