Triethylamine → HCID 73387936, compound

HRID 1056564Notes

Reaction equation

HRID 1056564 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:46][CH2:47]Cl)(=[O:45])[CH:42]([CH3:44])[CH3:43]>CN(C=O)C>[C:41]([O:46][CH2:47][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:45])[CH:42]([CH3:44])[CH3:43]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9989325CHLOROMETHYL ISOBUTYRATEHCID 42611257Vemurafenib

Product 1

HCID 73387936HCID 73387936, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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) and Et3N (57 μL, 0.4 mmol) in DMF (1 mL) was added chloromethyl isobutyrate (34 mg, 0.25 mmol) at rt. The reaction was stirred at rt for 16 h, then concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v)=4/1 to 3/1) to afford the title compound as a white solid (45 mg, 37.5%). The title compound was characterized by LC-MS and 1H NMR as shown below:

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (v/v)=4/1 to 3/1)

Sources & evidence

ORD record
ord-6cc45439bd8d417d8432b8275febc929
Source dataset
uspto-grants-2016_07
Patent number
US09399639B2

Reaction notes

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