N-[3-[1-[(4-fluorophenyl)methyl]-4-hydroxy-3-(3-methylbut-2-enyl)-6-oxo-2,3-dihydropyridin-5-yl]-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-7-yl]methanesulfonamide → N-[3-[1-[(4-fluorophenyl)methyl]-4-hydroxy-3-isopentyl-6-oxo-2,3-dihydropyridin-5-yl]-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-7-yl]methanesulfonamide

HRID 1172383Notes

Reaction equation

HRID 1172383 reaction equation
[F:1][C:2]1[CH:38]=[CH:37][C:5]([CH2:6][N:7]2[CH2:12][CH:11]([CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[C:10]([OH:18])=[C:9]([C:19]3[NH:24][C:23]4[CH:25]=[CH:26][C:27]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][C:22]=4[S:21](=[O:35])(=[O:34])[N:20]=3)[C:8]2=[O:36])=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:38]=[CH:37][C:5]([CH2:6][N:7]2[CH2:12][CH:11]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:10]([OH:18])=[C:9]([C:19]3[NH:24][C:23]4[CH:25]=[CH:26][C:27]([NH:29][S:30]([CH3:33])(=[O:31])=[O:32])=[CH:28][C:22]=4[S:21](=[O:34])(=[O:35])[N:20]=3)[C:8]2=[O:36])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 135949494N-[3-[1-[(4-fluorophenyl)methyl]-4-hydroxy-3-(3-methylbut-2-enyl)-6-oxo-2,3-dihydropyridin-5-yl]-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-7-yl]methanesulfonamide

Product 1

HCID 135949480N-[3-[1-[(4-fluorophenyl)methyl]-4-hydroxy-3-isopentyl-6-oxo-2,3-dihydropyridin-5-yl]-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-7-yl]methanesulfonamideYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-{3-[1-(4-fluoro-benzyl)-4-hydroxy-5-(3-methyl-but-2-enyl)-2-oxo-1,2,5,6-tetrahydro-pyridin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide (60 mg, 0.107 mmol) in ethyl acetate (2 mL) was treated with 5 wt % Pd/C (10 mg). The reaction was stirred under a hydrogen environment (1 atm) for 12 h and filtered through Celite. The filtrate was concentrated in vacuo to give N-{3-[1-(4-fluoro-benzyl)-4-hydroxy-5-(3-methyl-butyl)-2-oxo-1,2,5,6-tetrahydro-pyridin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide (54 mg, 90%) as a white solid. 1H NMR (400 MHz, CDCl3) δ: 0.78-0.83 (m, 6H), 0.95-1.12 (m, 2H), 1.31-1.45 (m, 2H), 1.64-1.73 (m, 1H), 2.50-2.55 (m, 1H), 3.06 (s, 3H), 3.18 (dd, 1H, J1=12.7 Hz, J2=4.3 Hz), 3.52 (dd, 1H, J1=12.9 Hz, J2=5.0 Hz), 4.31 (d, 1H, J=14.9 Hz), 4.93 (d, 1H, J=14.7 Hz), 6.84 (br s, 1H), 7.06 (t, 2H, J=8.6 Hz), 7.23-7.29 (m, 3H), 7.64 (dd, 1H, J1=8.7 Hz, J2=2.3 Hz), 7.68 (d, 1H, J=2.3 Hz). LC-MS (ESI) calculated for C25H29FN4O6S2: 564.7, found 565.5 [M+H+].

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d911d688638a45acbf7624a2763ecfd2
Source dataset
uspto-grants-2010_11
Patent number
US07834009B2

Reaction notes

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