Sodium Hydroxide → 6-(3-Chloro-4-fluoro-phenyl)-8-methyl-8-vinyl-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carboxylic acid

HRID 2047701노트

반응식

HRID 2047701 반응식
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[NH:11][CH:10]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[C:17]([Cl:22])[CH:16]=3)[CH2:9][C:8]([CH3:25])([CH:23]=[CH2:24])[C:7]=2[N:6]=1)=[O:4].[OH-].[Na+]>O1CCCC1.CO.O>[Cl:22][C:17]1[CH:16]=[C:15]([CH:10]2[CH2:9][C:8]([CH3:25])([CH:23]=[CH2:24])[C:7]3[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:14]=[CH:13][C:12]=3[NH:11]2)[CH:20]=[CH:19][C:18]=1[F:21]

참가 물질

6

반응물 2

HCID 14798Sodium HydroxideHCID 665877906-(3-Chloro-4-fluoro-phenyl)-8-methyl-8-vinyl-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carboxylic acid methyl ester

생성물 1

HCID 565916986-(3-Chloro-4-fluoro-phenyl)-8-methyl-8-vinyl-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carboxylic acid수율 64.9%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 6-(3-chloro-4-fluoro-phenyl)-8-methyl-8-vinyl-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carboxylic acid methyl ester (300 mg, 0.8 mmol) in tetrahydrofuran (2 mL) and methanol (2 mL) was added 3 N sodium hydroxide (1 mL). The reaction mixture was stirred at room temperature for 16 hours, and then diluted with water (10 mL), extracted with diethyl ether (20 mL). The organic layer was discarded. The aqueous layer was acidified with concentrated hydrochloric acid to pH 4 and extracted with ethyl acetate (40 mL×3), and the combined organics were dried over anhydrous Na2SO4. The solvent was removed in vacuo and purified by preparative HPLC to afford 6-(3-chloro-4-fluoro-phenyl)-8-methyl-8-vinyl-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carboxylic acid (180 mg, 62.7%) as a yellow oil. MS (ESI+) [(M+H)+] 347.2.

후처리

  1. extractionextracted with diethyl ether (20 mL)
  2. extractionextracted with ethyl acetate (40 mL×3)
  3. dry with materialthe combined organics were dried over anhydrous Na2SO4
  4. customThe solvent was removed in vacuo
  5. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-16cc73e65b2d44fcb72e48e1e96fc653
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592594B2

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