Water → 1-(2,3-dihydroxypropyl)-N-(4-fluoro-5-((4-bromo-2-chloro phenyl)amino)benzo[d]oxazol-6-yl)cyclopropane-1-sulfonamide

HRID 928987Notes

Reaction equation

HRID 928987 reaction equation
[CH2:1]([C:4]1([S:7]([NH:10][C:11]2[C:19]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=3[Cl:28])=[C:18]([F:29])[C:14]3[N:15]=[CH:16][O:17][C:13]=3[CH:12]=2)(=[O:9])=[O:8])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].C[N+]1([O-])CC[O:34]CC1.[OH2:38]>C1COCC1.[Os](=O)(=O)(=O)=O>[OH:38][CH:2]([CH2:3][OH:34])[CH2:1][C:4]1([S:7]([NH:10][C:11]2[C:19]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=3[Cl:28])=[C:18]([F:29])[C:14]3[N:15]=[CH:16][O:17][C:13]=3[CH:12]=2)(=[O:9])=[O:8])[CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 897047911-allyl-N-(4-fluoro-5-((4-bromo-2-chlorophenyl)amino)benzo[d]oxazol-6-yl)cyclopropane-1-sulfonamide

Product 1

HCID 716678101-(2,3-dihydroxypropyl)-N-(4-fluoro-5-((4-bromo-2-chloro phenyl)amino)benzo[d]oxazol-6-yl)cyclopropane-1-sulfonamideYield 28.2%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-allyl-N-(4-fluoro-5-((4-bromo-2-chlorophenyl)amino)benzo[d]oxazol-6-yl)cyclopropane-1-sulfonamide (100 mg, 0.38 mmol) in THF (10 mL) was added N-methylmorpholine-N-oxide (44 mg, 0.38 mmol) followed by osmium tetraoxide (10 mg, 0.04 mmol) and water (0.5 mL). After stirring at room temperature overnight, the mixture was concentrated and then diluted with EA. The organic layer was washed with water, saturated NaHCO3 (aq.) and brine sequentially, dried over Na2SO4, filtered and concentrated to give a residue, which was purified by flash chromatography to give the product as white solid (30 mg, 28.2% yield). 1H NMR (400 MHz, CDCl3): δ 8.10 (s, 1H), 7.98 (s, 1H), 7.45-7.34 (m, 2H), 7.32-7.21 (m, 1H), 6.83 (s, 1H), 6.44-6.30 (m, 1H), 4.41-4.25 (m, 2H), 4.21-4.12 (m, 1H), 3.72-3.62 (m, 1H), 2.85-2.78 (m, 1H), 1.32-1.26 (m, 2H), 1.16-1.21 (m, 4H). MS APCI (+) m/z: 535.8, [M+H].

Workup

  1. concentrationthe mixture was concentrated
  2. additiondiluted with EA
  3. washThe organic layer was washed with water, saturated NaHCO3 (aq.) and brine sequentially
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue, which
  8. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-fbb2d3ca531a4193aa23a882edf10e15
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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