Acetone → HCID 11519283, compound

HRID 900168Notes

Reaction equation

HRID 900168 reaction equation
C([NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[NH:29][C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH:22][CH2:23][CH:24]4[CH2:28][CH2:27][CH2:26][O:25]4)[C:16]=3[C:15]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:10][CH:9]=1)(=[O:7])=[O:6])C=C.C[N+]1([O-])CC[O:40]CC1.[CH3:44][C:45]([CH3:47])=[O:46]>O.C(O)(C)(C)C.O=[Os](=O)(=O)=O>[OH:46][CH:45]([CH2:47][OH:40])[CH2:44][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[NH:29][C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH:22][CH2:23][CH:24]4[CH2:28][CH2:27][CH2:26][O:25]4)[C:16]=3[C:15]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:10][CH:9]=1)(=[O:7])=[O:6]

Participants

7

Reactant 3

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 11634563HCID 11634563, compound

Product 1

HCID 11519283HCID 11519283, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of 26 mg (0.1 mmol) of N-allyl-4-{5-phenyl-4-[(tetrahydro-furan-2-ylmethyl)-amino]-7H-pyrrolo[2,3-d]pyrimidin-6-yl}-benzenesulfonamide (Example 12) in 2.8 ml acetone and 1 ml water was treated with 62 μl (0.005 mmol) of a 2.5 wt. % solution of OsO4 in tert-butanol and 19 mg (0.2 mmol) of 4-methylmorpholine-N-oxide. The yellow solution was stirred at room temperature for 26 h, then was quenched with water (10 ml) and extracted with dichloromethane (3×). The combined organic layers were dried over Na2SO4, filtered, and the filtrate was purified by chromatography on silica gel (CH2Cl2:MeOH, 22:3) to give the title compound. 1H-NMR (DMSO-d6) δ 1.29-1.40 (m, 1 H), 1.53-1.84 (m, 3 H), 2.40-2.49 (m, 1 H), 2.53-2.63 (m, 1 H), 2.82-2.90 (m, 1 H), 3.21-3.59 (m, 6 H), 3.69-3.77 (m, 1 H), 4.51 (t, J=5.6 Hz, 1 H), 4.75 (d, J=5.1 Hz, 1 H), 4.97-5.03 (m, 1 H), 7.37-7.42 (m, 3 H), 7.44-7.53 (m, 5 H), 7.65 (d, J=8.5 Hz, 2 H), 8.21 (s, 1 H), 12.34 (br s, 1 H). Mass Spectrum (ESI) m/e=524.0 (M+1).

Workup

  1. customwas quenched with water (10 ml)
  2. extractionextracted with dichloromethane (3×)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customthe filtrate was purified by chromatography on silica gel (CH2Cl2:MeOH, 22:3)

Sources & evidence

ORD record
ord-a90845ac8d84468ab2b50ab1d2ced408
Source dataset
uspto-grants-2008_04
Patent number
US07358250B2

Reaction notes

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