Dimethylformamide → HCID 68917835, compound

HRID 1191291Notes

Reaction equation

HRID 1191291 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]1[CH:9]([NH:10][C:11]2[N:16]=[C:15](C3CCCCCC3)[CH:14]=[CH:13][N:12]=2)[CH2:8][CH2:7][CH2:6][N:5]1[CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.Br[CH2:31][CH2:32][O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+].[CH3:52][N:53]([CH3:56])C=O>>[N:53]1([C:15]2[CH:14]=[CH:13][N:12]=[C:11]([NH:10][CH:9]3[CH2:8][CH2:7][CH2:6][N:5]([CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)[CH:4]3[CH2:3][CH2:2][NH:1][CH2:31][CH2:32][O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[N:16]=2)[CH2:56][CH2:9][CH2:4][CH2:3][CH2:2][CH2:52]1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 68922440HCID 68922440, compound

Product 1

HCID 68917835HCID 68917835, compound

Procedure

N-[(2RS,3SR)-2-(2-aminoethyl)-1-cyclohexylpiperidin-3-yl]-4-cycloheptylpyrimidin-2-amine (75 mg), dimethylformamide (1 mL), (2-bromoethoxy)(tert-butyl)dimethylsilane (44 μL) and potassium carbonate (52 mg) were stirred at room temperature for overnight. The reaction solution was added aqueous saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and then concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:methanol:aqueous ammonia=70:27:3) to obtain the title compound (89 mg) having the following physical properties.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol:aqueous ammonia=70:27:3)

Sources & evidence

ORD record
ord-2c61bec256f94c239d39e2b485c043ee
Source dataset
uspto-grants-2014_03
Patent number
US08680092B2

Reaction notes

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