Hydrochloric Acid → 1-Biphenyl-2-ylmethyl-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carboxylic acid

HRID 1497671노트

반응식

HRID 1497671 반응식
C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:7]=1)=[O:5])C.O[Li].O.Cl>CO.O>[C:19]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][N:8]1[C:9]2[C:14](=[N:13][CH:12]=[CH:11][CH:10]=2)[C:15](=[O:16])[C:6]([C:4]([OH:5])=[O:3])=[CH:7]1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 867254331-Biphenyl-2-ylmethyl-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carboxylic acid ethyl ester

생성물 1

HCID 769024811-Biphenyl-2-ylmethyl-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carboxylic acid수율 11%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

To a stirred solution of 1-Biphenyl-2-ylmethyl-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carboxylic acid ethyl ester (6) (850 mg, 2.4 mmol) in MeOH (8 mL) was added LiOH—H2O (100.2 mg, 4.8 mmol) and stirred at RT for 16 h. After completion of the reaction, distilled-off the solvent from the reaction and diluted with water. The aqueous part was acidified with 2 N HCl, extracted with EtOAC and organic layer was washed with brine. It was dried over Na2SO4, concentrated and the residue was purified by Prep-HPLC to get 1-Biphenyl-2-ylmethyl-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carboxylic acid (7) (88 mg, 11%) as off white solid.

후처리

  1. customAfter completion of the reaction
  2. customdistilled-off the solvent from the reaction
  3. extractionextracted with EtOAC and organic layer
  4. washwas washed with brine
  5. dry with materialIt was dried over Na2SO4
  6. concentrationconcentrated
  7. customthe residue was purified by Prep-HPLC

출처 및 근거

ORD 기록
ord-c233f1a58f1c471e960124bd9b588459
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199987B2

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