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Hydrochloric Acid → 5-Chloro-2-piperazinyl-n-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-pyridine-4-carboxamide, hydrochloride salt

HRID 497014
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HRID 497014 반응식
[Cl:1]C1[CH:7]=[C:6]([C:8]([NH:10][CH2:11][C:12]23[CH2:21][CH:16]4[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]4)[CH2:13]2)[CH2:19]3)=[O:9])[C:5]([Cl:22])=[CH:4][N:3]=1.C(O[C:28]([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:22][C:5]1[C:6]([C:8]([NH:10][CH2:11][C:12]23[CH2:13][CH:14]4[CH2:15][CH:16]([CH2:17][CH:18]([CH2:20]4)[CH2:19]2)[CH2:21]3)=[O:9])=[CH:7][C:28]([N:30]2[CH2:31][CH2:32][NH:33][CH2:34][CH2:35]2)=[N:3][CH:4]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 11416492N-(1-adamantylmethyl)-2,5-dichloroisonicotinamide

생성물 1

HCID 102242375-Chloro-2-piperazinyl-n-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-pyridine-4-carboxamide, hydrochloride salt수율 51.8%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide
용매
HCID 887Methanol용매
HCID 312751,4-Dioxane용매

실험 절차

A solution of 2,5-dichloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-pyridine-4-carboxamide (0.30 g, Example 1a) and 1-t-butoxycarbonylpiperazine (0.344 g) in dimethylsulfoxide (3 ml) was heated at 160° C. for 40 min. 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 (0.195 g).

후처리

  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

출처 및 근거

ORD 기록
ord-d9337884d7c74167809713ac9b5a1bcd
출처 데이터셋
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06949539B2

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