Potassium Hydroxide → HCID 73388149, compound

HRID 1056574Notes

Reaction equation

HRID 1056574 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+].Cl[CH2:37][O:38][C:39](=[O:54])[CH2:40][CH:41]1[CH2:46][CH2:45][N:44](C(OC(C)(C)C)=O)[CH2:43][CH2:42]1>CN(C=O)C>[ClH:1].[NH:44]1[CH2:45][CH2:46][CH:41]([CH2:40][C:39]([O:38][CH2:37][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)=[O:54])[CH2:42][CH2:43]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 42611257VemurafenibHCID 86711092HCID 86711092, compound

Product 1

HCID 73388149HCID 73388149, compoundYield 126.2%

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) and a solution of tert-butyl 4-(2-(chloromethoxy)-2-oxoethyl)piperidine-1-carboxylate (60 mg, 0.2 mmol) in DMF (100 μL). The crude product was purified by a silica gel column chromatography (PE/EtOAc (v/v)=3/1 to 2/1) to afford the title compound as a white solid (86 mg, 56.6%). The title compound was characterized by LC-MS and 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)=3/1 to 2/1)

Sources & evidence

ORD record
ord-660df974e0c14cecba0da2f402022dbd
Source dataset
uspto-grants-2016_07
Patent number
US09399639B2

Reaction notes

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