Pyridine → [2-(7-Bromo-isoquinoline-5-sulfonylamino)-ethyl]-carbamic acid tert-butyl ester

HRID 2219198ノート

反応式

HRID 2219198 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([S:12](Cl)(=[O:14])=[O:13])[C:5]2[CH:6]=[CH:7][N:8]=[CH:9][C:10]=2[CH:11]=1.[C:16]([O:20][C:21](=[O:26])[NH:22][CH2:23][CH2:24][NH2:25])([CH3:19])([CH3:18])[CH3:17].N1C=CC=CC=1>C(Cl)Cl>[C:16]([O:20][C:21](=[O:26])[NH:22][CH2:23][CH2:24][NH:25][S:12]([C:4]1[C:5]2[CH:6]=[CH:7][N:8]=[CH:9][C:10]=2[CH:11]=[C:2]([Br:1])[CH:3]=1)(=[O:14])=[O:13])([CH3:19])([CH3:17])[CH3:18]

参加物

5

反応物 3

HCID 1049PyridineHCID 187201N-BOC-ethylenediamineHCID 588161467-Bromoisoquinoline-5-sulfonyl chloride

生成物 1

HCID 58816140[2-(7-Bromo-isoquinoline-5-sulfonylamino)-ethyl]-carbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

A slurry of 7-bromo-isoquinoline-5-sulfonyl chloride (16.3 g, 35.5 mmol) in CH2Cl2 (200 mL) is added in small portions to a stirred solution of (2-amino-ethyl)-carbamic acid tert-butyl ester (6 mL, 37.9 mmol) and pyridine (2.79 mL, 34.5 mmol) in CH2Cl2 (100 mL) at 0° C. under nitrogen. The resultant mixture is allowed to stir at ambient temperature overnight. The mixture is diluted with another 100 mL CH2Cl2, washed with saturated aqueous NaHCO3 (150 mL) solution, dried, filtered and concentrated. The dark oil is subject to column chromatography (Biotage 75 short; eluted with 10-20% CH3CN/CH2Cl2+0.2% NEt3) to give the title compound as a white solid. ESIMS: m/z 430 [(M+H)+, 79Br], 432 [(M+H)+, 81Br].

後処理

  1. washwashed with saturated aqueous NaHCO3 (150 mL) solution
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washThe dark oil is subject to column chromatography (Biotage 75 short; eluted with 10-20% CH3CN/CH2Cl2+0.2% NEt3)

出典と根拠

ORDレコード
ord-b389aa74b15448c4923b40c7644e820e
出典データセット
uspto-grants-2008_08
特許番号
US07414063B2

反応ノート

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