2-Methoxyethylamine → HCID 118036483, compound

HRID 1777944Notes

Reaction equation

HRID 1777944 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][N:8]=1>>[Cl:6][C:7]1[CH:12]=[C:11]([NH:5][CH2:4][CH2:3][O:2][CH3:1])[C:10]([C:14]([F:15])([F:16])[F:17])=[CH:9][N:8]=1.[Cl:13][C:11]1[C:10]([C:14]([F:17])([F:15])[F:16])=[CH:9][N:8]=[C:7]([NH:5][CH2:4][CH2:3][O:2][CH3:1])[CH:12]=1

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 457909412,4-Dichloro-5-(trifluoromethyl)pyridine

Product 2

HCID 118036483HCID 118036483, compoundHCID 118036790HCID 118036790, compound

Procedure

2-Methoxyethylamine (1.0 ml, 11.57 mmol) was added drop wise to 2,4-dichloro-5-(trifluoromethyl)pyridine (500 mg, 2.32 mmol) at 0° C. and the mixture stirred at room temperature for 2.5 h. The reaction mixture was partitioned between saturated aqueous NaHCO3 solution and DCM, the organic layer dried over Na2SO4 and evaporated. The residue was applied to a 120 g RediSep® silica column as a DCM solution and purified by normal phase chromatography, eluting with a gradient from DCM to 50% EtOAc in DCM. The title compound was obtained as the major regioisomer and elutes before the 4-chloro-N-(2-methoxyethyl)-5-(trifluoromethyl)pyridin-2-amine (ratio 2:1). Product containing fractions were combined and evaporated to give the title compound as a yellow-white solid. (UPLC-MS 6) tR 0.96; ESI-MS 255.1 [M+H]+.

Workup

  1. customThe reaction mixture was partitioned between saturated aqueous NaHCO3 solution and DCM
  2. dry with materialthe organic layer dried over Na2SO4
  3. customevaporated
  4. custompurified by normal phase chromatography
  5. washeluting with a gradient from DCM to 50% EtOAc in DCM

Sources & evidence

ORD record
ord-241b47c6f8ca42ee90514a38ee48c6ed
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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