Potassium Hydroxide → HCID 86711095, compound

HRID 1056582Notes

Reaction equation

HRID 1056582 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.[OH-].[K+].[C:36]([O:40][C:41]([NH:43][C:44]([CH3:51])([CH3:50])[C:45]([O:47][CH2:48]Cl)=[O:46])=[O:42])([CH3:39])([CH3:38])[CH3:37]>CN(C=O)C>[C:36]([O:40][C:41]([NH:43][C:44]([CH3:51])([CH3:50])[C:45]([O:47][CH2:48][N:14]1[C:11]2=[N:12][CH:13]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:9]=[C:10]2[C:16]([C:17](=[O:18])[C:19]2[C:24]([F:25])=[CH:23][CH:22]=[C:21]([NH:26][S:27]([CH2:30][CH2:31][CH3:32])(=[O:28])=[O:29])[C:20]=2[F:33])=[CH:15]1)=[O:46])=[O:42])([CH3:39])([CH3:38])[CH3:37]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 11776960150109-48-1HCID 42611257Vemurafenib

Product 1

HCID 86711095HCID 86711095, 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 (0.3 g, 0.61 mmol) in DMF (2.5 mL), KOH (69 mg, 0.4 mmol), and a solution of chloromethyl 2-((tert-butoxycarbonyl)amino)-2-methylpropanoate (158 mg, 0.61 mmol) in DMF (0.5 mL). The title compound was purified by a silica gel columnchromatography (PE/EtOAc (v/v)=4/1 to 3/1) and was obtained as a white solid (339 mg, 78.7%). 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 columnchromatography (PE/EtOAc (v/v)=4/1 to 3/1)

Sources & evidence

ORD record
ord-f505f0da4096488d817c1a679b6567ab
Source dataset
uspto-grants-2016_07
Patent number
US09399639B2

Reaction notes

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