Diisopropylethylamine → (2-[(1-Chloro-4-hydroxy-isoquinoline-3-carbonyl)-amino]-ethyl}-carbamic acid tert-butyl ester

HRID 523714

反応式

HRID 523714 の反応式
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13]([OH:15])=O)[N:3]=1.F[P-](F)(F)(F)(F)F.N1([O+]=C(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[C:40]([O:44][C:45](=[O:50])[NH:46][CH2:47][CH2:48][NH2:49])([CH3:43])([CH3:42])[CH3:41].C(N(C(C)C)C(C)C)C>ClCCl>[C:40]([O:44][C:45](=[O:50])[NH:46][CH2:47][CH2:48][NH:49][C:13]([C:4]1[N:3]=[C:2]([Cl:1])[C:11]2[C:6]([C:5]=1[OH:12])=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:15])([CH3:43])([CH3:41])[CH3:42]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamineHCID 110205201-Chloro-4-hydroxyisoquinoline-3-carboxylic acidHCID 178484681HCID 178484681、化合物

生成物 1

HCID 86595472(2-[(1-Chloro-4-hydroxy-isoquinoline-3-carbonyl)-amino]-ethyl}-carbamic acid tert-butyl ester収率 10.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a mixture of 45 mg (0.2 mmol) of 1-chloro-4-hydroxy-isoquinoline-3-carboxylic acid, 76 mg (0.2 mmol) of benzotriazol-1-yl-(bis-dimethylamino-methylene)-oxonium hexafluoro phosphate (HBTU), 32 μl (2-amino-ethyl)-carbamic acid tert-butyl ester (0.2 mmol), and 1 ml of dichloromethane was added 96 μl (0.55 mmol) of ethyl-diisopropyl-amine with stirring. Stirring was continued at ambient temperature for 5 days. The product was isolated from the reaction mixture by flash column chromatography on silica gel using hexanes:ethyl acetate (8:2) as the eluent to give a tan gum. 8 mg of the title compound were obtained; MS-(−)-ion: M−1=364.0.

後処理

  1. stirringStirring
  2. customThe product was isolated from the reaction mixture by flash column chromatography on silica gel
  3. customto give a tan gum

出典と根拠

ORDレコード
ord-92916928601f4eff89ba8f187748e700
出典データセット
uspto-grants-2016_05
特許番号
US09339527B2

関連ノート

読み込み中…