2-Methoxyethylamine → HCID 24760081, compound

HRID 1989677Notes

Reaction equation

HRID 1989677 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[CH:15]=[C:16]([S:20](Cl)(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=3)[N:9]=2)[CH:5]=[C:4]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[CH:3]=1.[CH3:34][O:35][CH2:36][CH2:37][NH2:38]>C1COCC1.CCOC(C)=O>[CH3:34][O:35][CH2:36][CH2:37][NH:38][S:20]([C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:10]2[N:9]=[C:8]([C:6]3[CH:5]=[C:4]([C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:26][CH:25]=4)[CH:3]=[C:2]([CH3:1])[N:7]=3)[CH:13]=[CH:12][CH:11]=2)[CH:15]=1)(=[O:22])=[O:21]

Participants

5

Reactant 2

HCID 80182-MethoxyethylamineHCID 866154503-[6'-Methyl-4'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-benzenesulfonyl chloride

Product 1

HCID 24760081HCID 24760081, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared from 3-[6′-methyl-4′-(4-trifluoromethyl-phenyl)-[2,2′]bipyridinyl-6-yl]-benzenesulfonyl chloride (example I.2) (0.300 g, 0.613 mmol) by treatment with commercially available 2-methoxyethylamine (0.138 mg, 1.84 mmol) in THF (5 mL) at 23° C. for 16 h. Diluted with EtOAc, washed with 5% citric acid, sat. NaHCO3-sol. and brine, dried organic layer over Na2SO4. Removal of the solvent in vacuum left a crude product, which was purified by silica gel column chromatography with EtOAc followed by trituration with diethyl ether/heptane to give the title compound (0.200 g, 62%) as a white solid. MS (ISP) 528.2 [(M+H)+]; mp 126° C.

Workup

  1. washwashed with 5% citric acid, sat. NaHCO3-sol
  2. customRemoval of the solvent in vacuum
  3. waitleft a crude product, which
  4. customwas purified by silica gel column chromatography with EtOAc

Sources & evidence

ORD record
ord-a21e855e8cda4e9b8dd4632c705463f8
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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