Triethylamine → HCID 73387015, compound

HRID 1056601Notes

Reaction equation

HRID 1056601 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.CCN(CC)CC.[C:41](=[O:52])([O:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[O:42][CH2:43]Cl>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].CN(C=O)C.CCOC(C)=O>[C:41](=[O:52])([O:45][C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)[O:42][CH2:43][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

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 14787053Carbonic acid, chloromethyl phenyl esterHCID 42611257Vemurafenib

Product 1

HCID 73387015HCID 73387015, compoundYield 7.8%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 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), TBAB (132 mg, 0.4 mmol) and Et3N (114 μL, 0.8 mmol) in DMF (1 mL) was added chloromethyl phenyl carbonate (46 mg, 0.25 mmol). The reaction was stirred at rt for 12 h, then diluted with EtOAc (40 mL) and filtered. The filtrate was concentrated in vacuo and the residue was purified by a silica gel column chromatography (PE/EtOAc (v/v)=4/1) to afford the title compound as a white solid (10 mg, 7.7%). The title compound was characterized by LCMS and 1H NMR as shown below:

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was purified by a silica gel column chromatography (PE/EtOAc (v/v)=4/1)

Sources & evidence

ORD record
ord-4699b59b8d78489980d875665766b720
Source dataset
uspto-grants-2016_07
Patent number
US09399639B2

Reaction notes

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