Lithium Hydroxide → 2-(Difluoromethyl)-5-(isobutyramidomethyl)nicotinic acid

HRID 1469797노트

반응식

HRID 1469797 반응식
[F:1][CH:2]([F:21])[C:3]1[N:13]=[CH:12][C:11]([CH2:14][NH:15][C:16](=[O:20])[CH:17]([CH3:19])[CH3:18])=[CH:10][C:4]=1[C:5]([O:7]CC)=[O:6].[Li+].[OH-]>O1CCOCC1.O>[F:21][CH:2]([F:1])[C:3]1[N:13]=[CH:12][C:11]([CH2:14][NH:15][C:16](=[O:20])[CH:17]([CH3:19])[CH3:18])=[CH:10][C:4]=1[C:5]([OH:7])=[O:6]

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 71059744Ethyl 2-(difluoromethyl)-5-(isobutyramidomethyl)nicotinate

생성물 1

HCID 710598402-(Difluoromethyl)-5-(isobutyramidomethyl)nicotinic acid수율 83.5%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of ethyl 2-(difluoromethyl)-5-(isobutyramidomethyl)nicotinate (200 mg, 0.66 mmol) in 1,4-Dioxane was added a solution of LiOH (70 mg, 1.66 mmol) in H2O (1 mL) and the reaction mixture was stirred at rt for 1 h. Then the reaction mixture was quenched with 1N HCl and the precipitated solid was filtered and dried to afford 150 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 13.98 (br s, 1H), 8.72 (s, 1H), 8.45 (t, 1H), 8.17 (s, 1H), 7.67-7.32 (t, J=54 Hz, 1H), 4.39-4.37 (d, J=5.7 Hz, 2H), 2.43 (m, 1H), 1.04-1.02 (d, J=6.6 Hz, 6H).

후처리

  1. customThen the reaction mixture was quenched with 1N HCl
  2. filtrationthe precipitated solid was filtered
  3. customdried

출처 및 근거

ORD 기록
ord-899338ff0e1a4ce2b13d6d88e2de94ca
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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