Potassium hydroxy sulfite → HCID 49869006, compound

HRID 570953Notes

Reaction equation

HRID 570953 reaction equation
[OH:1]OS([O-])=O.[K+].[O:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[C:16]1[N:17]=[CH:18][N:19]2[C:24](=[O:25])[N:23]([CH2:26][S:27][CH3:28])[N:22]=[N:21][C:20]=12>CN(C=O)C>[O:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[C:16]1[N:17]=[CH:18][N:19]2[C:24](=[O:25])[N:23]([CH2:26][S:27]([CH3:28])=[O:1])[N:22]=[N:21][C:20]=12

Participants

4

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 66831781HCID 66831781, compound

Product 1

HCID 49869006HCID 49869006, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An aqueous solution (250 μL) of Oxone™ (54 mg, 0.195 mmol) was added to a stirred solution of 8-(benzo[d]oxazol-2-yl)-3-(methylthiomethyl)imidazo[5,1-d][1,2,3,5]tetrazin-4(3H)-one (25 mg, 0.0795 mmol) in DMF (1 mL) and the resulting suspension was stirred overnight. The mixture was poured into ice (10 g) and the precipitate was filtered and washed successively with water, ethyl acetate and diethyl ether to give 19 mg of the title compound as a bright yellow solid (73% yield). δH (DMSO d6): 9.12 (1H, s), 7.89-7.94 (2H, m), 7.47-7.55 (2H, m), 5.66 (1H, d, J=13.2), 5.53 (1H, d, J=13.2), 2.80 (3H, s). LCMS: 97% pure at 4.63 min., m/z (ES+): 331.1 (MH+).

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed successively with water, ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-692a41c553864d8cb2df11361a8fe807
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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