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

HRID 601350Notes

Reaction equation

HRID 601350 reaction equation
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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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)−.

Workup

  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

Sources & evidence

ORD record
ord-b1dd66b3d7b844b085c27afef1e534f1
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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