Methyl morpholine oxide → N-(1-((6-(1,2-dihydroxyethyl)pyridin-2-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79289Notes

Reaction equation

HRID 79289 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=C(C=C)[N:26]=2)[N:4]=1)[CH3:2].C[N+]1([O-])CC[O:37]CC1.[CH3:41][C:42]([CH3:44])=[O:43].O>[Os](=O)(=O)(=O)=O>[OH:43][CH:42]([C:44]1[N:26]=[C:25]([CH2:24][N:5]2[C:6]3[C:11](=[C:10]([NH:12][C:13]([C:15]4[N:19]5[CH:20]=[CH:21][CH:22]=[CH:23][C:18]5=[N:17][CH:16]=4)=[O:14])[CH:9]=[CH:8][CH:7]=3)[C:3]([CH2:1][CH3:2])=[N:4]2)[CH:30]=[CH:29][CH:28]=1)[CH2:41][OH:37]

Participants

5

Reactant 3

HCID 82029Methyl morpholine oxideHCID 18366337Propan-2-one--water (1/1)HCID 67260793N-(3-ethyl-1-((6-vinylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 67260561N-(1-((6-(1,2-dihydroxyethyl)pyridin-2-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a solution of N-(3-ethyl-1-((6-vinylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (Example 24, Step B; 40 mg, 0.095 mmol) in acetone/water (2 mL/0.5 mL) was added N-methylmorpholine N-oxide (44 mg, 0.19 mmol), followed by osmium tetroxide (2.5% in tert-butanol, 15 μL). The mixture was stirred for 1 hour and then quenched by the addition of a saturated solution of sodium thiosulfate (1 mL). The mixture was concentrated under reduced pressure to remove acetone and diluted with dichloromethane and saturated sodium chloride solution (5 mL). The phases were separated and the aqueous was extracted with dichloromethane/isopropanol (10:1; 2×10 mL). The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure to give the product (40 mg).

Workup

  1. customquenched by the addition of a saturated solution of sodium thiosulfate (1 mL)
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto remove acetone
  4. additiondiluted with dichloromethane and saturated sodium chloride solution (5 mL)
  5. customThe phases were separated
  6. extractionthe aqueous was extracted with dichloromethane/isopropanol (10:1; 2×10 mL)
  7. dry with materialThe combined organic phases were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-491aab06422b488ab4fec3db10993333
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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