HCID 136403700, compound → 4-Hydroxy-3-(7-hydroxy-1,1-dioxido-4h-1,2,4-benzothiadiazin-3-yl)-1-methyl-1-propylnaphthalen-2(1h)-one

HRID 2224828Notes

Reaction equation

HRID 2224828 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])[C:21]([CH3:33])([CH2:30][CH2:31][CH3:32])[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.[Pd]>[OH:29][C:28]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([CH3:33])([CH2:30][CH2:31][CH3:32])[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

4

Reactant 1

HCID 136403700HCID 136403700, compound

Product 1

HCID 1363971684-Hydroxy-3-(7-hydroxy-1,1-dioxido-4h-1,2,4-benzothiadiazin-3-yl)-1-methyl-1-propylnaphthalen-2(1h)-oneYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of Example 26G (1.44 g, 2.87 mmol) in tetrahydrofuran (40 mL) was treated with 10% palladium on carbon (0.145 g, 10% weight) and stirred at 25° C. under a hydrogen balloon for 72 hours. The vessel was purged with nitrogen gas and the mixture was filtered through celite. The filtrate was concentrated in vacuo to give the title compound (0.732 g, 62%). 1H NMR (300 MHz, DMSO-d6): δ ppm 0.63 (m, 4 H) 0.89 (m, 1 H) 1.57 (m, 3 H) 2.01 (m, 1 H) 2.19 (m, 1 H) 7.17 (m, 2 H) 7.55 (m, 2 H) 7.75 (m, 2 H) 8.15 (m, 1 H) 10.37 (m, 1 H) 13.71 (m, 1 H). MS (ESI−) m/z 411 (M−H)−.

Workup

  1. customThe vessel was purged with nitrogen gas
  2. filtrationthe mixture was filtered through celite
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-63f371e228af43a182b9c7ea3e0edf9c
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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