Acetone → HCID 16679490, compound

HRID 2232985Notes

Reaction equation

HRID 2232985 reaction equation
[N:1]1([C:8]2[C:13]([CH2:14][NH:15][C:16]3[N:20]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=4[Cl:28])[CH:19]=[N:18][N:17]=3)=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:29][C:30]([CH3:32])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl>[Cl:28][C:22]1[C:23]([Cl:27])=[CH:24][CH:25]=[CH:26][C:21]=1[N:20]1[CH:19]=[N:18][N:17]=[C:16]1[NH:15][CH2:14][C:13]1[C:8]([N:1]2[CH2:7][CH2:6][CH2:5][N:4]([CH:30]([CH3:32])[CH3:29])[CH2:3][CH2:2]2)=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 68705957HCID 68705957, compound

Product 1

HCID 16679490HCID 16679490, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of Example 113A in 1,2-dichloroethane (10 ml) was added acetone (3 mL) and sodium triacetoxyborohydride (253 mg, 1.194 mmol). The reaction mixture was stirred at room temperature overnight. Saturated sodium bicarbonate was added and the layers were separated. The aqueous layer was extracted with dichloromethane. The combined organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash column chromatography using dichloromethane/methanol (80:20) to give the title compound. MS (ESI+) m/z 460.6 (M+H)+; Rt=1.47. 1H NMR (DMSO-d6) δ 8,171 (s, 1H); 8,049 (d, 1H); 7,831(d, 1H); 7,586(m, 3H); 6,837 (dd, 1H); 6,521 (t, 1H); 4,353 (d, 2H); 3,377 (m, 4H); 3,289 (m, 1H); 2,862 (m, 2H); 2,642 (m, 2H); 1,773 (m, 2H); 0,949 (m, 6H).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-48aeac2fbc594ef69588e7f2c8c4cf9f
Source dataset
uspto-grants-2010_05
Patent number
US07709469B2

Reaction notes

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