Ammonium formate → 4-hydroxy-3-(7-hydroxy-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-1-(propylamino)quinolin-2(1H)-one

HRID 601350노트

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HRID 601350 반응식
C([O:8][C:9]1[CH:36]=[CH:35][C:12]2[NH:13][C:14]([C:19]3[C:20](=[O:34])[N:21]([NH:30][CH2:31][CH2:32][CH3:33])[C:22]4[C:27]([C:28]=3[OH:29])=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:15][S:16](=[O:18])(=[O:17])[C:11]=2[CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>O1CCCC1.[OH-].[Pd+2].[OH-].[Pd]>[OH:29][C:28]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]([NH:30][CH2:31][CH2:32][CH3:33])[C:20](=[O:34])[C:19]=1[C:14]1[NH:13][C:12]2[CH:35]=[CH:36][C:9]([OH:8])=[CH:10][C:11]=2[S:16](=[O:17])(=[O:18])[N:15]=1

참가 물질

6

반응물 2

HCID 2723923Ammonium formateHCID 1363584153-[7-(benzyloxy)-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl]-4-hydroxy-1-(propylamino)quinolin-2(1H)-one

생성물 1

HCID 1363584174-hydroxy-3-(7-hydroxy-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-1-(propylamino)quinolin-2(1H)-one수율 100%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 9942167Palladium hydroxide촉매HCID 8028Tetrahydrofuran용매

실험 절차

The product of Example 358B (0.020 g, 0.04 mmol) in tetrahydrofuran (5 mL) was treated with ammonium formate (13 mg, 0.19 mmole), palladium hydroxide (2 mg) and 10% Pd/C (1 mg) and the resulting mixture was refluxed for 1 hour. The catalyst was filtered off and the filtrate evaporated to give a white solid. The solid residue was partitioned between ethyl acetate (100 mL) and water (5 mL). The layers were separated and the organic solvent was removed under reduced pressure to give the title compound (0.016 g, 100%). MS (ESI−) m/z 413 (M−H)−.

후처리

  1. temperaturethe resulting mixture was refluxed for 1 hour
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate evaporated
  4. customto give a white solid
  5. customThe solid residue was partitioned between ethyl acetate (100 mL) and water (5 mL)
  6. customThe layers were separated
  7. customthe organic solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-b1dd66b3d7b844b085c27afef1e534f1
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902203B2

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