Potassium Hydroxide → HCID 73388038, compound

HRID 1056568Notes

Reaction equation

HRID 1056568 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+].[CH:36]1([C:41]([O:43][CH:44](Cl)[CH3:45])=[O:42])[CH2:40][CH2:39][CH2:38][CH2:37]1>CN(C=O)C>[CH:36]1([C:41]([O:43][CH:44]([N:14]2[C:11]3=[N:12][CH:13]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)[CH:9]=[C:10]3[C:16]([C:17](=[O:18])[C:19]3[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]=3[F:33])=[CH:15]2)[CH3:45])=[O:42])[CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 22595339HCID 22595339, compoundHCID 42611257Vemurafenib

Product 1

HCID 73388038HCID 73388038, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The title compound was prepared according to the procedure as described in Example 12 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, 1.23 mmol) and a solution of 1-chloroethyl cyclopentanecarboxylate (108 mg, 0.61 mmol) in anhydrous DMF (0.5 mL). The curde product was purified by a silica gel column chromatography (PE/EtOAc (v/v)=5/1) and recrystallized in PE to give the title compound as a white solid (147 mg, 38%). The title compound was characterized by LC-MS and 1H NMR as shown below:

Workup

  1. customThe title compound was prepared
  2. customThe curde product was purified by a silica gel column chromatography (PE/EtOAc (v/v)=5/1)
  3. customrecrystallized in PE

Sources & evidence

ORD record
ord-b92015769a864a829b39c678d6cce526
Source dataset
uspto-grants-2016_07
Patent number
US09399639B2

Reaction notes

Loading…