Sodium Dithionite → HCID 19437742, compound

HRID 1734530Notes

Reaction equation

[CH2:1]([O:8][C:9]1[N:10]=[N:11][CH:12]=[C:13]2[C:17]([N+:18]([O-])=O)=[C:16]([CH3:21])[N:15]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38]>CO.O>[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38].[NH2:18][C:17]1[C:13]2[C:14](=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[N:10]=[N:11][CH:12]=2)[N:15]([CH2:22][CH:23]([CH3:24])[CH3:25])[C:16]=1[CH3:21]

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of 1.0 g (2.94 mmol) of 7-benzyloxy-1-isobutyl-2-methyl-3-nitropyrrolo [2,3-d]pyridazine in 30 ml of methanol is treated with a solution of 2.6 g (14.6 mmol) of sodium dithionite in 30 ml of water and stirred at 70° C. for 30 min. After addition of 100 ml of water, the mixture is extracted with 3×100 ml of ethyl acetate. The organic extracts are washed with 200 ml of water, dried over magnesium sulfate and subsequently treated with a solution of 341 mg (2.94 mmol) of fumaric acid in 10 ml of methanol. The solution is subsequently concentrated to a volume of 30 ml. After filtration, 800 mg (64%) of the title compound are isolated. M.p.: 143° C. (dec.).

Workup

extractionthe mixture is extracted with 3×100 ml of ethyl acetate
washThe organic extracts are washed with 200 ml of water
dry with materialdried over magnesium sulfate
concentrationThe solution is subsequently concentrated to a volume of 30 ml
filtrationAfter filtration, 800 mg (64%) of the title compound
customare isolated

Sources & evidence

ORD record: ord-58564a1ea33c4994bc3b0b5acbeab9cc
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05534515

Reaction notes

Loading…