3-[7-(benzyloxy)-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl]-1-(cyclobutylamino)-4-hydroxyquinolin-2(1H)-one → 1-(cyclobutylamino)-4-hydroxy-3-(7-hydroxy-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)quinolin-2(1H)-one

HRID 601282Notes

Reaction equation

HRID 601282 reaction equation
C([O:8][C:9]1[CH:37]=[CH:36][C:12]2[NH:13][C:14]([C:19]3[C:20](=[O:35])[N:21]([NH:30][CH:31]4[CH2:34][CH2:33][CH2:32]4)[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>O1CCCC1.[Pt]=O>[CH:31]1([NH:30][N:21]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:28]([OH:29])=[C:19]([C:14]3[NH:13][C:12]4[CH:36]=[CH:37][C:9]([OH:8])=[CH:10][C:11]=4[S:16](=[O:17])(=[O:18])[N:15]=3)[C:20]2=[O:35])[CH2:32][CH2:33][CH2:34]1

Participants

4

Reactant 1

HCID 1363740373-[7-(benzyloxy)-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl]-1-(cyclobutylamino)-4-hydroxyquinolin-2(1H)-one

Product 1

HCID 1363741731-(cyclobutylamino)-4-hydroxy-3-(7-hydroxy-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)quinolin-2(1H)-oneYield 102.3%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

The product of Example 304H (0.059 g, 0.11 mmol) in tetrahydrofuran (4 mL) was reacted with platinum oxide (50 mg) under hydrogen atmosphere at 25° C. for 20 hours. The catalyst was filtered off and the filtrate evaporated to give the title compound (0.048 g, 100%). MS (ESI−) m/z 425 (M−H)−.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-7e324e1d4dbf48f4a5741f9c16c76ec1
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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