m-Chloroperbenzoic acid → (4R)-tert-butyl 4-((3-carbamoyl-6-(5-(methylsulfinyl)-1,3,4-oxadiazol-2-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-3,3-dimethylpiperidine-1-carboxylate

HRID 877748Notes

Reaction equation

HRID 877748 reaction equation
[C:1]([C:4]1[CH:9]=[N:8][N:7]2[CH:10]=[C:11]([C:13]3[O: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[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][C:22]1([CH3:35])[CH3:34])(=[O:3])[NH2:2].C1C=C(Cl)C=C(C(OO)=[O:44])C=1>C(Cl)(Cl)Cl>[C:1]([C:4]1[CH:9]=[N:8][N:7]2[CH:10]=[C:11]([C:13]3[O:14][C:15]([S:18]([CH3:19])=[O:44])=[N:16][N:17]=3)[CH:12]=[C:6]2[C:5]=1[NH:20][C@@H:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][C:22]1([CH3:35])[CH3:34])(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 68350378(R)-tert-butyl 4-((3-carbamoyl-6-(5-(methylthio)-1,3,4-oxadiazol-2-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-3,3-dimethylpiperidine-1-carboxylate

Product 1

HCID 68291350(4R)-tert-butyl 4-((3-carbamoyl-6-(5-(methylsulfinyl)-1,3,4-oxadiazol-2-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-3,3-dimethylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of (R)-tert-butyl 4-((3-carbamoyl-6-(5-(methylthio)-1,3,4-oxadiazol-2-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-3,3-dimethylpiperidine-1-carboxylate (306 mg, 0.610 mmol) and mCPBA (265 mg, 1.182 mmol) in chloroform (6 mL) was stirred at room temperature for 2 h. Additional mCPBA (78 mg) was added. After one more hour at room temperature, the staring material was consumed. The crude solution was taken to the next reaction without purification. MS (ES+) m/z: 518.3 (M+H).

Workup

  1. customAfter one more hour at room temperature, the staring material was consumed
  2. customThe crude solution was taken to the next reaction without purification

Sources & evidence

ORD record
ord-24b6d88cdcb84e6fb8e438253d7eb81f
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

Loading…