2-Amino-5-bromobenzenesulfonamide → N-[2-(aminosulfonyl)-4-bromophenyl]-1-benzyl-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamide

HRID 601124

반응식

HRID 601124 반응식
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][N:16]=2)[C:11]([OH:18])=[C:10]([C:19](OCC)=[O:20])[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][C:27]=1[S:33]([NH2:36])(=[O:35])=[O:34]>C1(C)C=CC=CC=1>[NH2:36][S:33]([C:27]1[CH:28]=[C:29]([Br:32])[CH:30]=[CH:31][C:26]=1[NH:25][C:19]([C:10]1[C:9](=[O:24])[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:17]2[C:12]([C:11]=1[OH:18])=[CH:13][CH:14]=[CH:15][N:16]=2)=[O:20])(=[O:35])=[O:34]

참가 물질

4

반응물 2

HCID 8207002-Amino-5-bromobenzenesulfonamideHCID 54729304Ethyl 1-benzyl-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

생성물 1

HCID 67063612N-[2-(aminosulfonyl)-4-bromophenyl]-1-benzyl-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamide수율 70%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

The product of Example 84B (0.065 g, 0.20 mmol) was reacted with the product of Example 84A (0.050 g, 0.20 mmol) in toluene (4 mL) at reflux for 3 hours. The reaction was cooled and the resulting precipitate was collected by filtration and dried to give to give the title compound as an off-white solid (0.074 g, 70%). MS (ESI+) m/z 528.9 (M+H)+, 530.9 (M+H)+, 551.1 (M+Na)+, 552.9 (M+Na)+; 1H NMR (300 MHz, DMSO-d6) δ 5.67 (s, 2H), 7.23 (m, 2H), 7.29 (m, 3H), 7.48 (dd, J=8.09, 4.78 Hz, 1H), 7.69 (s, 2H), 7.87 (dd, J=8.82, 2.21 Hz, 1H), 7.97 (m, 1H), 8.01 (d, J=2.21 Hz, 1H), 8.55 (dd, J=7.91, 1.65 Hz, 1H), 8.82 (dd, J=4.60, 1.65 Hz, 1H), 12.44 (s, 1H), 16.45 (s, 1H).

후처리

  1. temperatureat reflux for 3 hours
  2. temperatureThe reaction was cooled
  3. filtrationthe resulting precipitate was collected by filtration
  4. customdried
  5. customto give

출처 및 근거

ORD 기록
ord-a4404f8bb2454edf8350a8338aa14f28
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902203B2

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