Triethylamine → 7-[4-(t-Butoxycarbonylaminomethyl)-2-isoindolinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester

HRID 1494820노트

반응식

HRID 1494820 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[N:10][C:11](Cl)=[C:12]([F:17])[CH:13]=2)[N:8]([CH:19]2[CH2:21][CH2:20]2)[CH:7]=1)=[O:5])[CH3:2].[C:22]([O:26][C:27]([NH:29][CH2:30][C:31]1[CH:39]=[CH:38][CH:37]=[C:36]2[C:32]=1[CH2:33][NH:34][CH2:35]2)=[O:28])([CH3:25])([CH3:24])[CH3:23].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[N:10][C:11]([N:34]3[CH2:33][C:32]4[C:36](=[CH:37][CH:38]=[CH:39][C:31]=4[CH2:30][NH:29][C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])[CH2:35]3)=[C:12]([F:17])[CH:13]=2)[N:8]([CH:19]2[CH2:21][CH2:20]2)[CH:7]=1)=[O:5])[CH3:2]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 11722954Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylateHCID 198284894-(t-Butyloxycarbonylaminomethyl)isoindoline

생성물 1

HCID 538742897-[4-(t-Butoxycarbonylaminomethyl)-2-isoindolinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester수율 80%

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

A mixture of 310 mg of 1-cyclopropyl-6-fluoro-7- chloro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester, 524 mg of 4-(t-butyloxycarbonylaminomethyl)isoindoline, 0.42 ml of triethylamine, and 5 ml of anhydrous chloroform was heated at 60°-70° C. for 0.5 hours while stirring. The resulting reaction mixture was diluted with 25 ml of chloroform. The mixture was washed with 5% acetic acid and brine in this order, dried over anhydrous sodium sulfate, and condensed. The residue was crystallized by the addition of ethylether. The crystals were collected by filtration and recrystallized from a mixed solvent of chloroform, methanol, and ethanol to obtain 417 mg of 7-[4- (t-butoxycarbonylaminomethyl)-2-isoindolinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester.

후처리

  1. temperaturewas heated at 60°-70° C. for 0.5 hours
  2. customThe resulting reaction mixture
  3. washThe mixture was washed with 5% acetic acid and brine in this order
  4. dry with materialdried over anhydrous sodium sulfate, and condensed
  5. customThe residue was crystallized by the addition of ethylether
  6. filtrationThe crystals were collected by filtration
  7. customrecrystallized from a mixed solvent of chloroform, methanol, and ethanol

출처 및 근거

ORD 기록
ord-c76fbd78718342b69aa0fa87ef5f1fe5
출처 데이터셋
uspto-grants-1991_06
특허 번호
US05026856

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