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

HRID 250369
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HRID 250369 반응식
[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]
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참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamineHCID 110205201-Chloro-4-hydroxyisoquinoline-3-carboxylic acidHCID 178484681HCID 178484681, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-f6a10703af2d492aa3a34425deacbe6e
출처 데이터셋
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07863292B2

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