Water → HCID 178456579, compound

HRID 892103Notes

Reaction equation

HRID 892103 reaction equation
[ClH:1].[Cl:2][CH2:3][CH:4]1[CH2:15][N:14]2[C:6]([C:7]3[NH:8][C:9]([CH:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)=[N:10][C:11]=3[N:12]([CH2:17][CH2:18][CH3:19])[C:13]2=[O:16])=[N:5]1.[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.O>CS(C)=O>[ClH:2].[ClH:1].[CH:20]1([C:9]2[NH:8][C:7]3[C:6]4=[N:5][CH:4]([CH2:3][N:25]5[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]5)[CH2:15][N:14]4[C:13](=[O:16])[N:12]([CH2:17][CH2:18][CH3:19])[C:11]=3[N:10]=2)[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 962WaterHCID 8082PiperidineHCID 178456575HCID 178456575, compound

Product 1

HCID 178456579HCID 178456579, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

Compound 26 (49 mg, 0.14 mmol) obtained in Example 26 was dissolved in dimethyl sulfoxide (5 mL), to the solution was added piperidine (100 μL, 1.01 mmol, 7.2 equivalents), and the mixture was stirred with heating at 80° C. for 3.5 hours. To the reaction solution was added water, the mixture was extracted with ethyl acetate, and the extract was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (chloroform:methanol=95:5), to the product was added a 4 mol/L solution of hydrogen chloride in ethyl acetate, then the mixture was concentrated. The residue was crystallized from acetone to obtain the title compound (31 mg, 48%) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe extract was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (chloroform:methanol=95:5), to the product
  6. additionwas added a 4 mol/L solution of hydrogen chloride in ethyl acetate
  7. concentrationthe mixture was concentrated
  8. customThe residue was crystallized from acetone

Sources & evidence

ORD record
ord-38bbb1ca82374cfca920118b631a3623
Source dataset
uspto-grants-2006_02
Patent number
US07005430B2

Reaction notes

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