Sodium Hydroxide → 1,1-dibutyl-4-hydroxy-3-[7-(hydroxymethyl)-1,1-dioxido-4H-thieno[2,3-e][1,2,4]thiadiazin-3-yl]-2(1H)-naphthalenone

HRID 494472Notes

Reaction equation

[CH2:1]([C:5]1([CH2:33][CH2:34][CH2:35][CH3:36])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]2[NH:21][C:20]3[S:22][CH:23]=[C:24]([CH2:25][O:26]COC)[C:19]=3[S:18](=[O:31])(=[O:30])[N:17]=2)[C:6]1=[O:32])[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>Cl.O1CCOCC1>[CH2:1]([C:5]1([CH2:33][CH2:34][CH2:35][CH3:36])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]2[NH:21][C:20]3[S:22][CH:23]=[C:24]([CH2:25][OH:26])[C:19]=3[S:18](=[O:31])(=[O:30])[N:17]=2)[C:6]1=[O:32])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of the product of Example 10F (27 mg, 0.051 mmol) in 4.0 N HCl in dioxane (4 mL) was stirred at 25° C. for 18 hours and concentrated in vacuo. A suspension of the residue in acetonitrile (2 mL) was treated with 1.0 N sodium hydroxide solution (51 μL, 0.051 mmol) and stirred at 25° C. for 1 h. The solution was lyophilized to afford the title compound (28 mg, 100%). 1H NMR (300 MHz, DMSO-d6): δ 16.82 (m, 1 H), 8.04 (d, J=7.35 Hz, 1 H), 7.47 (m, 2 H), 7.32 (t, J=7.35 Hz, 1 H), 6.95 (s, 1 H), 5.32 (t, J=5.70 Hz, 1H), 4.61 (m, 2 H), 2.09 (m, 2 H), 1.70 (m, 2 H), 1.02 (m, 4 H), 0.84 (m, 2 H), 0.67 (m, 6 H), 0.49 (s, 2 H).

Workup

concentrationconcentrated in vacuo
additionA suspension of the residue in acetonitrile (2 mL)

Sources & evidence

ORD record: ord-03dc4a1c59e74dbfbb52cf4e8959999f
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538105B2

Reaction notes

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