Potassium Hydroxide → HCID 86711100, compound

HRID 1056587Notes

Reaction equation

HRID 1056587 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][CH:44]([CH:51]([CH3:53])[CH3:52])[C:45]([O:47][CH:48](Cl)[CH3:49])=[O:46])=[O:42])([CH3:39])([CH3:38])[CH3:37]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:16]([C:17](=[O:18])[C:19]4[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]=4[F:33])=[CH:15][N:14]([CH:48]([O:47][C:45](=[O:46])[CH:44]([NH:43][C:41]([O:40][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:42])[CH:51]([CH3:52])[CH3:53])[CH3:49])[C:11]3=[N:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 42611257VemurafenibHCID 867110991-Chloroethyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate

Product 1

HCID 86711100HCID 86711100, compoundYield 65%

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 anhydrous DMF (2.5 mL), KOH (69 mg, 1.22 mmol) and a solution of 1-chloroethyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate (172 mg, 0.61 mmol) in anhydrous DMF (0.5 mL). The crude product was purified by a silica gel column chromatography (PE/EtOAc (v/v)=4/1 to 3/1) to afford the title compound as orange oil (0.29 g, 65%). The title compound was characterized by 1H NMR as shown below:

Workup

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

Sources & evidence

ORD record
ord-94eb571fcad54c98a53877052a5fb3eb
Source dataset
uspto-grants-2016_07
Patent number
US09399639B2

Reaction notes

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