Hydrochloric Acid → HCID 10295969, compound

HRID 497017Notes

Reaction equation

HRID 497017 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9]([NH:11][CH2:12][C:13]23[CH2:22][CH:17]4[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]4)[CH2:14]2)[CH2:20]3)=[O:10])[CH:5]=[CH:4][N:3]=1.C(OC([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)=O)(C)(C)C.Cl>CS(C)=O.CO.O1CCOCC1>[ClH:1].[Cl:8][C:7]1[C:2]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[N:3][CH:4]=[CH:5][C:6]=1[C:9]([NH:11][CH2:12][C:13]12[CH2:20][CH:19]3[CH2:21][CH:15]([CH2:16][CH:17]([CH2:18]3)[CH2:22]1)[CH2:14]2)=[O:10]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 21906731HCID 21906731, compound

Product 1

HCID 10295969HCID 10295969, compoundYield 26.6%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2,3-dichloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-pyridine-4-carboxamide (0.15 g, Example 10a) and 1-t-butoxycarbonylpiperazine (0.19 g) in dimethylsulfoxide (2 ml) was heated at 100° C. for 8 hours. The solution was cooled and partitioned between saturated aqueous sodium bicarbonate solution and dichloromethane and the organic layer dried over magnesium sulphate. Concentration in vacuo and chromatography on silica gave a colourless solid. This was redissolved in methanol and treated with 4M HCl in dioxan (4 ml). Once deprotection was complete the solution was partially concentrated in vacuo then diluted slowly with diethyl ether with rapid stirring. The resulting white precipitate was filtered, washed with diethyl ether and dried to afford the title compound (0.050 g).

Workup

  1. temperatureThe solution was cooled
  2. custompartitioned between saturated aqueous sodium bicarbonate solution and dichloromethane
  3. dry with materialthe organic layer dried over magnesium sulphate
  4. concentrationConcentration in vacuo and chromatography on silica
  5. customgave a colourless solid
  6. concentrationwas partially concentrated in vacuo
  7. additionthen diluted slowly with diethyl ether with rapid stirring
  8. filtrationThe resulting white precipitate was filtered
  9. washwashed with diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-a69045a84612480593790682331e213d
Source dataset
uspto-grants-2005_09
Patent number
US06949539B2

Reaction notes

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