Sodium borohydride → 3-(4-hydroxycyclohexyl)-2-(10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-N-(1-methyl-1H-pyrazol-3-yl)propionamide

HRID 14991Notes

Reaction equation

HRID 14991 reaction equation
[CH3:1][N:2]1[C:15]2[CH:14]=[C:13]([CH:16]([CH2:26][CH:27]3[CH2:32][CH2:31][C:30](=[O:33])[CH2:29][CH2:28]3)[C:17]([NH:19][C:20]3[CH:24]=[CH:23][N:22]([CH3:25])[N:21]=3)=[O:18])[CH:12]=[CH:11][C:10]=2[S:9](=[O:35])(=[O:34])[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[BH4-].[Na+]>CO>[OH:33][CH:30]1[CH2:31][CH2:32][CH:27]([CH2:26][CH:16]([C:13]2[CH:12]=[CH:11][C:10]3[S:9](=[O:35])(=[O:34])[C:8]4[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=4)[N:2]([CH3:1])[C:15]=3[CH:14]=2)[C:17]([NH:19][C:20]2[CH:24]=[CH:23][N:22]([CH3:25])[N:21]=2)=[O:18])[CH2:28][CH2:29]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 24864113HCID 24864113, compound

Product 1

HCID 250094483-(4-hydroxycyclohexyl)-2-(10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-N-(1-methyl-1H-pyrazol-3-yl)propionamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

50 mg of 2-(10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-N-(1-methyl-1H-pyrazol-3-yl)-3-(4-oxocyclohexyl)propionamide are suspended in 20 ml of methanol, and 3.8 mg of sodium borohydride are added at room temperature. The mixture is stirred at room temperature for another hour. During the duration of the reaction, a clear solution slowly forms. The methanol is removed under reduced pressure, and the residue is extracted with ethyl acetate and water. The organic phase is washed twice with water and then dried over MgSO4 and concentrated under reduced pressure. The residue is lyophilized. This gives 42 mg of 3-(4-hydroxycyclohexyl)-2-(10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-N-(1-methyl-1H-pyrazol-3-yl)propionamide as a white amorphous solid.

Workup

  1. customDuring the duration of the reaction
  2. customThe methanol is removed under reduced pressure
  3. extractionthe residue is extracted with ethyl acetate and water
  4. washThe organic phase is washed twice with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-259e2f79c5ee4441b6af173430a08c49
Source dataset
uspto-grants-2010_06
Patent number
US07732440B2

Reaction notes

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