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

反応式

HRID 601124 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-a4404f8bb2454edf8350a8338aa14f28
出典データセット
uspto-grants-2011_03
特許番号
US07902203B2

関連ノート

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