Sodium Hydroxide → 4-(5-Azido-isoquinoline-6-yloxy)-piperidin-1-carboxylic acid tert-butyl ester

HRID 1022860노트

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HRID 1022860 반응식
[OH-].[Na+].N1CCC[C@H]1C(O)=O.[N-:11]=[N+:12]=[N-:13].[Na+].[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([O:28][C:29]2[C:30](I)=[C:31]3[C:36](=[CH:37][CH:38]=2)[CH:35]=[N:34][CH:33]=[CH:32]3)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>CS(C)=O.[Cu]I.O>[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([O:28][C:29]2[C:30]([N:11]=[N+:12]=[N-:13])=[C:31]3[C:36](=[CH:37][CH:38]=2)[CH:35]=[N:34][CH:33]=[CH:32]3)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

참가 물질

8

반응물 4

HCID 14798Sodium Hydroxide2회HCID 33557Sodium Azide2회HCID 145742L-Proline2회HCID 576467514-(5-Iodo-isoquinoline-6-yloxy)-piperidin-1-carboxylic acid tert-butyl ester

생성물 1

HCID 576467494-(5-Azido-isoquinoline-6-yloxy)-piperidin-1-carboxylic acid tert-butyl ester수율 100.2%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

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온도
60 °C

실험 절차

Under argon atmosphere 40 μL (0.04 mmol) of 1N NaOH, 4.6 mg (0.04 mmol) of L-proline, 3.8 mg of (0.02 mmol) CuI and 15.6 mg (0.24 mmol) of NaN3 were added to a solution of 91 mg (0.2 mmol) of 4-(5-iodo-isoquinoline-6-yloxy)-piperidin-1-carboxylic acid tert-butyl ester (12) in 2 mL of DMSO. The mixture was heated to 60° C. for 18 h. NaN3, NaOH and L-proline were added in the same amounts again and the reaction was heated to 60° C. for 5 h. After cooling to room temperature water was added. The precipitate was filtered, washed with water and dried in vacuo to give 74 mg of compound 17, which was used without any additional purification.

후처리

  1. temperaturethe reaction was heated to 60° C. for 5 h
  2. additionwas added
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried in vacuo

출처 및 근거

ORD 기록
ord-19da6248913a41e5acdb0365862b6db0
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722671B2

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