Hydrochloric Acid → HCID 23577268, compound

HRID 1827143Notes

Reaction equation

HRID 1827143 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][NH:18][C:19]2[C:24]([Cl:25])=[C:23](SC)[N:22]=[C:21](SC)[N:20]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.Cl>C(O)C.[Ni]>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([CH2:17][NH:18][C:19]2[C:24]([Cl:25])=[CH:23][N:22]=[CH:21][N:20]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 23577287HCID 23577287, compound

Product 1

HCID 23577268HCID 23577268, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

4-[(5-Chloro-2,6-bis-methylsulfanyl-pyrimidin-4-ylamino)-methyl]-piperidine-1-carboxylic acid benzyl ester (1.0 g, 2.2 mmol) was suspended in ethanol (15 mL) and ethyl acetate added to give a homogeneoussolhution, and excess Raney nickel was added. The resulting reaction mixture was stirred overnight. More Raney Nickel was added and the reaction mixture was heated to 80° C. for 3 h. The mixture was filtered and the solids were washed with hot ethanol/ethyl acetate several times. The organics were concentrated and the resulting residue was purified by silica gel chromatography (isopropanol/methylene chloride). The product was dissolved in ether and treated with ethereal HCl (2.2 mmol) to form the HCl salt which was collected by filtration. The resulting 4-[(5-chloro-pyrimidin-4-ylamino)-methyl]-piperidine-1-carboxylic acid benzyl ester hydrochloride salt was collected by filtration as a colorless solid.

Workup

  1. additionwas added
  2. customThe resulting reaction mixture
  3. filtrationThe mixture was filtered
  4. washthe solids were washed with hot ethanol/ethyl acetate several times
  5. concentrationThe organics were concentrated
  6. customthe resulting residue was purified by silica gel chromatography (isopropanol/methylene chloride)
  7. dissolutionThe product was dissolved in ether

Sources & evidence

ORD record
ord-a437af80d8b94207877e057654b8c174
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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