Potassium hydroxy sulfite → HCID 49869140, compound

HRID 570957Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[N:11]=[CH:12][N:13]2[C:18](=[O:19])[N:17]([CH2:20][S:21][CH3:22])[N:16]=[N:15][C:14]=12.[OH:23]OS([O-])=O.[K+]>CN(C=O)C.O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[N:11]=[CH:12][N:13]2[C:18](=[O:19])[N:17]([CH2:20][S:21]([CH3:22])=[O:23])[N:16]=[N:15][C:14]=12

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. solution of 8-(benzo[d]thiazol-2-yl)-3-(methylthiomethyl)imidazo[5,1-d][1,2,3,5]tetrazin-4(3H)-one (0.23 mmol, 75 mg, 1 eq.) in DMF (4.5 mL) was added slowly drop wise Oxone™ (0.25 mmol, 77 mg, 1.1 eq.) dissolved in water (0.75 mL). The formed suspension was stirred at 0° C. and stepwise additions of Oxone™ in water were made until reaction completion. The reaction mixture was filtered and the obtained solid washed with water, acetonitrile, ethyl acetate and ether, and dried under vacuum to give the title compound. Yield: 98%. δH (DMSO-d6) 9.07 (1H, s), 8.22 (1H, m), 8.16 (1H, m), 7.60 (1H, m), 7.52 (1H, m), 5.63 (1H, d, J=13.2), 5.50 (1H, d, J=13.2), 2.79 (3H, s).

Workup

filtrationThe reaction mixture was filtered
washthe obtained solid washed with water, acetonitrile, ethyl acetate and ether
customdried under vacuum

Sources & evidence

ORD record: ord-ebc8aa29289b404fb0ed8ac4af332388
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024018B2

Reaction notes

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