Triacetoxyperiodinane → 5-Cyclopropyl-N-methyl-2-(5-methylpyridin-2-yl)-6-[(methylsulfonyl)(2-oxoethyl)amino]-2H-indazole-3-carboxamide

HRID 2202572Notes

Reaction equation

HRID 2202572 reaction equation
[CH:1]1([C:4]2[C:12]([N:13]([CH2:18][CH2:19][OH:20])[S:14]([CH3:17])(=[O:16])=[O:15])=[CH:11][C:10]3[C:6](=[C:7]([C:28]([NH:30][CH3:31])=[O:29])[N:8]([C:21]4[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][N:22]=4)[N:9]=3)[CH:5]=2)[CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:1]1([C:4]2[C:12]([N:13]([S:14]([CH3:17])(=[O:15])=[O:16])[CH2:18][CH:19]=[O:20])=[CH:11][C:10]3[C:6](=[C:7]([C:28]([NH:30][CH3:31])=[O:29])[N:8]([C:21]4[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][N:22]=4)[N:9]=3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 71766520HCID 71766520, compound

Product 1

HCID 866989535-Cyclopropyl-N-methyl-2-(5-methylpyridin-2-yl)-6-[(methylsulfonyl)(2-oxoethyl)amino]-2H-indazole-3-carboxamideYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of Compound (2) (278 mg) in DCM (6 mL) was added Dess-Martin periodinane (400 mg, 0.94 mmol). The mixture was stirred at room temperature for 1 h and then diluted with DCM (10 mL) and washed with aq. saturated NaHCO3 solution (10 mL) and water (10 mL). The organic phase was filtered to remove insoluble impurities, dried (MgSO4) and concentrated in vacuo to afford (i) (276 mg) which was used in the next step without further purification. ESI-MS m/z calculated for [M+MeOH]+: 474.2; found: 474.2.

Workup

  1. washwashed with aq. saturated NaHCO3 solution (10 mL) and water (10 mL)
  2. filtrationThe organic phase was filtered
  3. customto remove insoluble impurities
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-559bd95d28fc4f679deb2937cf716a90
Source dataset
uspto-grants-2016_06
Patent number
US09365554B2

Reaction notes

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