Potassium hydroxy sulfite → HCID 86707723, compound

HRID 1408990Notes

Reaction equation

HRID 1408990 reaction equation
[C:1]([C:4]1[CH:9]=[N:8][N:7]2[CH:10]=[C:11]([C:13]3[S:14][C:15]([S:18][CH3:19])=[N:16][N:17]=3)[CH:12]=[C:6]2[C:5]=1[NH:20][C@@H:21]1[CH2:25][CH2:24][C@@:23]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:26])[C:22]1([CH3:36])[CH3:35])(=[O:3])[NH2:2].[OH:37]OS([O-])=O.[K+]>CC(C)=O.O>[C:1]([C:4]1[CH:9]=[N:8][N:7]2[CH:10]=[C:11]([C:13]3[S:14][C:15]([S:18]([CH3:19])=[O:37])=[N:16][N:17]=3)[CH:12]=[C:6]2[C:5]=1[NH:20][C@@H:21]1[CH2:25][CH2:24][C@@:23]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:26])[C:22]1([CH3:36])[CH3:35])(=[O:3])[NH2:2]

Participants

5

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 86707724HCID 86707724, compound

Product 1

HCID 86707723HCID 86707723, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

A solution of tert-butyl ((1S,3R)-3-((3-carbamoyl-6-(5-(methylthio)-1,3,4-thiadiazol-2-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-1,2,2-trimethylcyclopentyl)carbamate (306.2 mg, 0.576 mmol) and oxone (531 mg, 0.864 mmol) in acetone (3 mL) and water (3 mL) was stirred at RT for 4 hrs. The reaction mixture was diluted with 30 mL of water which was stirred for 30 minutes. The solid was collected to give the desired tert-butyl ((1S,3R)-3-((3-carbamoyl-6-(5-(methylsulfinyl)-1,3,4-thiadiazol-2-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-1,2,2-trimethylcyclopentyl)carbamate (264.5 mg, 77% yield). MS (ES+) m/z: 548.08 (M+H); HPLC retention time: 3.296 min (analytical HPLC Method F).

Workup

  1. customThe solid was collected

Sources & evidence

ORD record
ord-e845d4636f464a0c864eda9715cceed8
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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