Hydrochloric Acid → N-(3-Ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-3-[2-(2-methoxy-ethylamino)-6-trifluoromethyl-pyridin-3-yl]-acrylamide

HRID 2265984Notes

Reaction equation

HRID 2265984 reaction equation
Cl[C:2]1[C:7]([CH:8]=[CH:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[C:18]([F:20])[C:17]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[C:16]([C:26]#[CH:27])[CH:15]=2)=[O:11])=[CH:6][CH:5]=[C:4]([C:28]([F:31])([F:30])[F:29])[N:3]=1.[CH3:32][O:33][CH2:34][CH2:35][NH2:36].Cl>O>[C:26]([C:16]1[CH:15]=[C:14]([CH:19]=[C:18]([F:20])[C:17]=1[NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH2:13][NH:12][C:10](=[O:11])[CH:9]=[CH:8][C:7]1[C:2]([NH:36][CH2:35][CH2:34][O:33][CH3:32])=[N:3][C:4]([C:28]([F:31])([F:30])[F:29])=[CH:5][CH:6]=1)#[CH:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 80182-MethoxyethylamineHCID 743823853-(2-Chloro-6-trifluoromethyl-pyridin-3-yl)-N-(3-ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-acrylamide

Product 1

HCID 74382536N-(3-Ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-3-[2-(2-methoxy-ethylamino)-6-trifluoromethyl-pyridin-3-yl]-acrylamideYield 12%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(2-chloro-6-trifluoromethyl-pyridin-3-yl)-N-(3-ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-acrylamide (30 mg, 0.28 mmol) and 2-methoxyethylamine (100 μl) was stirred at ambient temperature for 48 hrs. The reaction mixture was diluted with water and then acidified with 2N HCl solution. The aqueous phase was extracted with EtOAc and the combined organic phase was washed with brine, dried over anhydrous MgSO4 and concentrated under reduced pressure. The resulting residue was purified by column chromatography (Hex/EtOAc=2/3) to give the title compound (4.0 mg, 12%).

Workup

  1. extractionThe aqueous phase was extracted with EtOAc
  2. washthe combined organic phase was washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by column chromatography (Hex/EtOAc=2/3)

Sources & evidence

ORD record
ord-a0e28dd993b54ca9b716d9d4ebc9dd9c
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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