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Triethylamine → benzyl 2-((2-amino-3-carbamoylphenyl)carbamoyl)-3,4-dihydroquinoline-1(2H)-carboxylate

HRID 1895549
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HRID 1895549 반응식
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH:9]1[C:18]([OH:20])=O)=[O:7])([CH3:4])(C)C.CCN=C=NCCCN(C)C.Cl.[CH:33]1[CH:34]=[CH:35]C2N(O)N=N[C:37]=2[CH:38]=1.C(N(CC)CC)C.[NH2:50][C:51]1[C:59]([NH2:60])=[CH:58][CH:57]=[CH:56][C:52]=1[C:53]([NH2:55])=[O:54]>CN(C=O)C>[NH2:50][C:51]1[C:52]([C:53](=[O:54])[NH2:55])=[CH:56][CH:57]=[CH:58][C:59]=1[NH:60][C:18]([CH:9]1[CH2:10][CH2:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]1[C:6]([O:5][CH2:1][C:4]1[CH:35]=[CH:34][CH:33]=[CH:38][CH:37]=1)=[O:7])=[O:20]
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참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 104870292,3-DiaminobenzamideHCID 198232051-((Tert-butoxy)carbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid

생성물 1

HCID 66889373
benzyl 2-((2-amino-3-carbamoylphenyl)carbamoyl)-3,4-dihydroquinoline-1(2H)-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
55 °C

실험 절차

Step-1: To a solution of 1-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid (100 mg, 0.36 mmol) in anhydrous DMF (3 ml) was added EDC.HCl (207 mg, 1.08 mmol), HOBt (73.4 mg, 0.54 mmol) and triethylamine (0.08 ml, 0.54 mmol) at RT and the mixture was stirred for 10 min. To this reaction mixture, 2,3-diaminobenzamide (60 mg, 0.4 mmol) was added and heated to 55° C. over night. The reaction mixture was poured into ice cold water and stirred for 30 min. The precipitate formed was filtered and dried under vacuum to yield benzyl 2-((2-amino-3-carbamoylphenyl)carbamoyl)-3,4-dihydroquinoline-1(2H)-carboxylate. MS (ES+): m/z 2411.30 [M+H]+

후처리

  1. additionThe reaction mixture was poured into ice cold water
  2. stirringstirred for 30 min
  3. customThe precipitate formed
  4. filtrationwas filtered
  5. customdried under vacuum

출처 및 근거

ORD 기록
ord-adf4f784edd146439a48b92993e8d7c6
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08513433B2

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