3-[7-(benzyloxy)-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl]-4-hydroxy-1,1-dipropyl-2(1H)-naphthalenone → HCID 135436704, compound

HRID 2224768Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A suspension of the compound of Example 2F (110 mg, 0.21 mmol) in 1:1:1 tetrahydrofuran-ethyl acetate-methanol (20 mL) was treated with 10% palladium on carbon (30 mg) and stirred at 25° C. under hydrogen atmosphere for 18 hours. The mixture was filtered through celite® and the filtrate concentrated in vacuo to afford the title compound (86 mg, 94%). 1H NMR (300 MHz, DMSO-d6): δ 13.87 (m, 1 H), 10.33 (s, 2 H), 8.15 (d, J=7.72 Hz, 1 H), 7.72 (m, 2 H), 7.52 (m, 2 H), 7.16 (m, 2 H), 2.15 (m, 2 H), 1.97 (m, J=11.77 Hz, 2 H), 0.89 (m, 2 H), 0.60 (m, 8 H).

Workup

filtrationThe mixture was filtered through celite®
concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record: ord-6e549a06d30f448db9257d9fdb1de69e
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378414B2

Reaction notes

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