Hydrochloric Acid → 4-(7-Propyl-isoquinolin-6-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 404744노트

반응식

HRID 404744 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([S:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][C:24]=2Cl)[CH:21]=[N:20][CH:19]=[CH:18]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1C(=O)[CH2:30][CH2:29][CH2:28]1.C([Mg]Cl)CC.Cl>C1COCC1.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.[Fe].C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([S:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][C:24]=2[CH2:28][CH2:29][CH3:30])[CH:21]=[N:20][CH:19]=[CH:18]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 592908234-(7-Chloro-isoquinolin-6-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl esterHCID 178455855HCID 178455855, 화합물

생성물 1

HCID 592906304-(7-Propyl-isoquinolin-6-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 3

HCID 11110968Iron (III) acetylacetonate촉매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

To 200 mg (0.52 mmol) 4-(7-Chloro-isoquinolin-6-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester (274) dissolved in 5 ml THF and 1 ml NMP were added 20 mg (0.055 mmol) Ferric (III) acetylacetonate. To the red solution 0.3 ml of propylmagnesium-chloride (2M in THF) were added and 2 min stirred at RT. 1 ml 1N HCl and 20 ml diethyl ether were added and the organic layer was washed with brine. The organic phases were dried over Sodium sulfate and evaporated. The residue was purified by HPLC. 85 mg of 4-(7-Propyl-isoquinolin-6-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester could be obtained as the trifluoroacetate.

후처리

  1. washthe organic layer was washed with brine
  2. dry with materialThe organic phases were dried over Sodium sulfate
  3. customevaporated
  4. customThe residue was purified by HPLC

출처 및 근거

ORD 기록
ord-d8b47be0070647619a4d67840443e4c8
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748614B2

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