N-[2-(aminosulfonyl)-4-bromophenyl]-1-benzyl-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamide → 1-benzyl-3-(1,1-dioxido-4H-pyrido[3,2-e][1,2,4]thiadiazin-3-yl)-4-hydroxy-1,8-naphthyridin-2(1H)-one

HRID 601131노트

반응식

HRID 601131 반응식
[NH2:1][S:2]([C:5]1[C:10]([NH:11][C:12]([C:14]2[C:15](=[O:32])[N:16]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:17]3[C:22]([C:23]=2[OH:24])=[CH:21][CH:20]=[CH:19][N:18]=3)=O)=[CH:9][CH:8]=[CH:7][N:6]=1)(=[O:4])=[O:3].NS(C1C=C(Br)C=CC=1NC(C1C(=O)N(CC2C=CC=CC=2)C2C(C=1O)=CC=CN=2)=O)(=O)=O>>[CH2:25]([N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][N:18]=2)[C:23]([OH:24])=[C:14]([C:12]2[NH:11][C:10]3[CH:9]=[CH:8][CH:7]=[N:6][C:5]=3[S:2](=[O:4])(=[O:3])[N:1]=2)[C:15]1=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

3

반응물 2

HCID 67063612N-[2-(aminosulfonyl)-4-bromophenyl]-1-benzyl-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamideHCID 67063943N-[2-(aminosulfonyl)pyridin-3-yl]-1-benzyl-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamide

생성물 1

HCID 1354643461-benzyl-3-(1,1-dioxido-4H-pyrido[3,2-e][1,2,4]thiadiazin-3-yl)-4-hydroxy-1,8-naphthyridin-2(1H)-one

실험 절차

The title compound was prepared according to the procedure of Example 84D substituting the product of Example 100A for the product of Example 84C to give after purification by reverse phase HPLC (water/acetonitrile/0.1% NH4OAc gradient) the title compound as a white solid (0.053 g, 10%). MS (ESI−) m/z 432 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 5.70 (m, 2H), 7.25 (m, 7H), 7.50 (dd, J=7.91, 4.60 Hz, 1H), 7.80 (dd, J=8.46, 4.41 Hz, 1H), 8.17 (d, J=8.46 Hz, 1H), 8.60 (m, J=5.79, 1.88, 1.88 Hz, 1H), 8.68 (dd, J=4.41, 1.10 Hz, 1H), 8.82 (dd, J=4.78, 1.84 Hz, 1H).

후처리

  1. customto give
  2. customafter purification by reverse phase HPLC (water/acetonitrile/0.1% NH4OAc gradient) the title compound as a white solid (0.053 g, 10%)

출처 및 근거

ORD 기록
ord-842ad780ed174ab5b35bd50bbdf4ca79
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902203B2

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