Water → HCID 71668126, compound

HRID 929033Notes

Reaction equation

HRID 929033 reaction equation
C(C1([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][S:17][C:13]=3[CH:12]=2)(=[O:9])=[O:8])CC1)C=C.C[N+]1([O-])CCO[CH2:33][CH2:32]1.[OH2:38].[CH2:39]1[CH2:43][O:42][CH2:41][CH2:40]1>[Os](=O)(=O)(=O)=O>[Br:27][C:24]1[CH:25]=[CH:26][C:21]([NH:20][C:19]2[C:11]([NH:10][S:7]([C:41]3([CH2:40][CH:39]([OH:38])[CH2:43][OH:42])[CH2:33][CH2:32]3)(=[O:8])=[O:9])=[CH:12][C:13]3[S:17][CH:16]=[N:15][C:14]=3[C:18]=2[F:29])=[C:22]([Cl:28])[CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 89704796HCID 89704796, compound

Product 1

HCID 71668126HCID 71668126, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a solution of 1-allyl-N-(5-((4-bromo-2-chlorophenyl)amino)-4-fluorobenzo[d]thiazol-6-yl)cyclopropane-1-sulfonamide (50 mg, 0.10 mmol) in THF (10 mL) was added N-methylmorpholine-N-oxide (12 mg, 0.1 mmol) followed by osmium tetraoxide (5 mg, 0.02 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 (25 mg, 46.9% yield). 1H NMR (400 MHz, CDCl3) δ 8.67 (s, 1H), 7.96 (s, 1H), 7.92 (d, 1H), 7.73 (d, 1H), 7.44 (m, 1H), 6.82 (s, 1H), 6.68 (s, 1H), 4.42-4.25 (m, 2H), 4.21-4.13 (m, 1H), 3.73-3.62 (m, 1H), 3.61-3.51 (m, 1H), 2.63-2.52 (m, 2H), 0.91-0.83 (m, 4H). MS APCI (+) m/z: 551.9, [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-f1f0265ca2aa430ebce78aad740a07d1
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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