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

HRID 1022860ノート

反応式

HRID 1022860 の反応式
[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]

参加物

8

反応物 4

HCID 14798Sodium Hydroxide2 回HCID 33557Sodium Azide2 回HCID 145742L-Proline2 回HCID 576467514-(5-Iodo-isoquinoline-6-yloxy)-piperidin-1-carboxylic acid tert-butyl ester

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-19da6248913a41e5acdb0365862b6db0
出典データセット
uspto-grants-2014_05
特許番号
US08722671B2

反応ノート

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