Triethylamine → HCID 73387721, compound

HRID 1056556Notes

Reaction equation

HRID 1056556 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]([C:19]4[C:20]([F:33])=[C:21]([NH:26][S:27]([CH2:30][CH2:31][CH3:32])(=[O:29])=[O:28])[CH:22]=[CH:23][C:24]=4[F:25])=[O:18])=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)=[CH:4][CH:3]=1.Cl[C:35]([O:37][CH2:38][CH3:39])=[O:36].C(N(CC)CC)C>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]([C:19]4[C:20]([F:33])=[C:21]([N:26]([S:27]([CH2:30][CH2:31][CH3:32])(=[O:28])=[O:29])[C:35](=[O:36])[O:37][CH2:38][CH3:39])[CH:22]=[CH:23][C:24]=4[F:25])=[O:18])=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 42611257Vemurafenib

Product 1

HCID 73387721HCID 73387721, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of N-(3-(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)-propane-1-sulfonamide (0.2 g, 0.41 mmol) in dioxane (15 mL) were added ethyl chloroformate (EtOCOCl, 44 mg, 0.41 mmol) and triethylamine (0.14 g, 1.38 mmol). The reaction was stirred at rt for 1.5 h, then concentrated in vacuo. The residue was purified by a silica gel column chromatography (hexane/EtOAc (v/v)=4/1) to afford the title compound as a white solid (0.12 g, 50%). The title compound was characterized by LC-MS and 1H NMR as shown below:

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by a silica gel column chromatography (hexane/EtOAc (v/v)=4/1)

Sources & evidence

ORD record
ord-32cc9fbee5df4396b96274274a5616f3
Source dataset
uspto-grants-2016_07
Patent number
US09399639B2

Reaction notes

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