Methyl 2-benzyl-9-bromo-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate → Methyl 5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate hydrobromide

HRID 521418

반응식

HRID 521418 반응식
C([N:8]1[CH2:17][C:16]2[NH:15][C:14]3[C:18]([Br:26])=[CH:19][CH:20]=[C:21]([C:22]([O:24][CH3:25])=[O:23])[C:13]=3[C:12](=[O:27])[C:11]=2[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[BrH:26].[O:27]=[C:12]1[C:11]2[CH2:10][CH2:9][NH:8][CH2:17][C:16]=2[NH:15][C:14]2[CH:18]=[CH:19][CH:20]=[C:21]([C:22]([O:24][CH3:25])=[O:23])[C:13]1=2

참가 물질

5

반응물 2

HCID 89657401Methyl 2-benzyl-9-bromo-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 89657238Methyl 5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate hydrobromide수율 65.1%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

To a solution of methyl 2-benzyl-9-bromo-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate (6.6 g, 15.4 mmol) in MeOH (100 mL) was added Pd/C (3.0 g, 5%, 50% water), the mixture was stirred at atmosphere of hydrogen for about 6.0 h. Then the mixture was filtered, washed with MeOH (20 mL). The filtrate was concentrated and the residue was recrystallized with MeOH (2.5 mL) to afford the product (3.4 g, 65%) as a white solid. 1H NMR (DMSO-d6) δ 12.0 (s, 1H), 9.18 (s, 1H), 7.61-7.72 (m, 2H), 7.22-7.23 (m, 1H), 4.32 (s, 2H), 3.81 (s, 3H), 3.38-3.40 (m, 2H), and 2.66-2.67 (m, 2H).

후처리

  1. filtrationThen the mixture was filtered
  2. washwashed with MeOH (20 mL)
  3. concentrationThe filtrate was concentrated
  4. customthe residue was recrystallized with MeOH (2.5 mL)

출처 및 근거

ORD 기록
ord-7021bedf28204cc9b63209ef73a65e68
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328111B2

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