Triethylamine → HCID 73387725, compound

HRID 1056560Notes

Reaction equation

HRID 1056560 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.C(N(CC)CC)C.Cl.[C:42](Cl)(=[O:49])[C:43]1[CH:48]=[CH:47][CH:46]=[N:45][CH:44]=1>C(Cl)(Cl)Cl>[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]([N:26]([S:27]([CH2:30][CH2:31][CH3:32])(=[O:28])=[O:29])[C:42](=[O:49])[C:43]5[CH:48]=[CH:47][CH:46]=[N:45][CH:44]=5)[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

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 42611257Vemurafenib

Product 1

HCID 73387725HCID 73387725, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The title compound was prepared according to the procedure as described in Example 3 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), triethylamine (228 μL, 1.6 mmol) and nicotinoyl chloride hydrochloride (146 mg, 0.2 mmol) in CHCl3 (10 mL). The crude product was purified by a silica gel column chromatography (PE/EtOAc (v/v)=2/1) to afford the title compound as a white solid (35 mg, 28.9%). 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)=2/1)

Sources & evidence

ORD record
ord-62489f0a82854605853f2d7e5553a8e0
Source dataset
uspto-grants-2016_07
Patent number
US09399639B2

Reaction notes

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