Hydrogen Peroxide → HCID 69284244, compound

HRID 2201090Notes

Reaction equation

HRID 2201090 reaction equation
[N:1]1[N:2]([C:6]2[CH:7]=[C:8]([NH:12][C:13]3[N:21]=[C:20]([NH:22][C@@H:23]4[CH2:28][CH2:27][CH2:26][CH2:25][C@@H:24]4[NH:29]C(OC(C)(C)C)=O)[C:19]([C:37]#[N:38])=[CH:18][C:14]=3[C:15]([NH2:17])=[O:16])[CH:9]=[CH:10][CH:11]=2)[N:3]=[CH:4][CH:5]=1.C([O-])([O-])=[O:40].[K+].[K+].OO.O>CS(C)=O>[N:1]1[N:2]([C:6]2[CH:7]=[C:8]([NH:12][C:13]3[C:14]([C:15]([NH2:17])=[O:16])=[CH:18][C:19]([C:37]([NH2:38])=[O:40])=[C:20]([NH:22][C@@H:23]4[CH2:28][CH2:27][CH2:26][CH2:25][C@@H:24]4[NH2:29])[N:21]=3)[CH:9]=[CH:10][CH:11]=2)[N:3]=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 67774643HCID 67774643, compound

Product 1

HCID 69284244HCID 69284244, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-(3-(2H-1,2,3-triazol-2-yl)phenylamino)-6-((1R,2S)-2-tert-butyloxycarbonylaminocyclohexylamino)-5-cyanonicotinamide (50 mg, 0.12 mmol) in DMSO (1 mL) was added K2CO3 (200 mg, 1.45 mmol) and H2O2 (50% in H2O, 0.8 mL) at ambient temperature (caution: gas evolution). After stirring for 5 min, it was added water, the resulting precipitate was collected by filtration and was treated with TFA in DCM, 10 min later, the solution was concentrated and purified by preparative HPLC to give 2-(3-(2H-1,2,3-triazol-2-yl)phenylamino)-6-((1R,2S)-2-aminocyclohexylamino)pyridine-3,5-dicarboxamide (20 mg). MS found for C26H33N9O4 as M+H, 436.4. λ=267.6, 312.8 nm.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. additionwas treated with TFA in DCM, 10 min later
  3. concentrationthe solution was concentrated
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-ec2c7880cf314c709724b2a7c446c8a0
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Reaction notes

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