Potassium Hydroxide → HCID 178449825, compound

HRID 1056576Notes

Reaction equation

HRID 1056576 reaction equation
Cl[C:2]1C=CC(C2C=C3C(C(C4C(F)=C(NS(CCC)(=O)=O)C=CC=4F)=O)=CNC3=NC=2)=CC=1.[OH-].[K+].[C:36]([O:40][C:41]([NH:43][CH:44]([CH:50]([CH3:52])[CH3:51])[C:45]([O:47]CCl)=[O:46])=[O:42])([CH3:39])([CH3:38])[CH3:37]>CN(C=O)C>[C+4:2].[C:36]([O:40][C:41]([NH:43][CH:44]([CH:50]([CH3:52])[CH3:51])[C:45]([O-:47])=[O:46])=[O:42])([CH3:39])([CH3:38])[CH3:37].[C:36]([O:40][C:41]([NH:43][CH:44]([CH:50]([CH3:52])[CH3:51])[C:45]([O-:47])=[O:46])=[O:42])([CH3:39])([CH3:38])[CH3:37].[C:36]([O:40][C:41]([NH:43][CH:44]([CH:50]([CH3:52])[CH3:51])[C:45]([O-:47])=[O:46])=[O:42])([CH3:39])([CH3:38])[CH3:37].[C:36]([O:40][C:41]([NH:43][CH:44]([CH:50]([CH3:52])[CH3:51])[C:45]([O-:47])=[O:46])=[O:42])([CH3:39])([CH3:38])[CH3:37]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 18629485HCID 18629485, compoundHCID 42611257Vemurafenib

Product 1

HCID 178449825HCID 178449825, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The title compound was prepared according to the procedure as described in Example 14 Step 2 using N-(3-(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)propane-1-sulfonamide (0.1 g, 0.2 mmol) in DMF (0.9 mL), KOH (23 mg, 0.4 mmol), a solution of chloromethyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate (54 mg, 0.2 mmol) in DMF (100 μL). The title compound was purified by a silica gel column chromatography (PE/EtOAc (v/v)=4/1 to 3/1) and was obtained as a white solid (82 mg, 55.8%). The title compound was characterized by LC-MS and 1H NMR as shown below:

Workup

  1. customThe title compound was purified by a silica gel column chromatography (PE/EtOAc (v/v)=4/1 to 3/1)

Sources & evidence

ORD record
ord-6761f468016e41519a1c3407fcfe1494
Source dataset
uspto-grants-2016_07
Patent number
US09399639B2

Reaction notes

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