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

HRID 601129Notes

Reaction equation

HRID 601129 reaction equation
[NH2:1][S:2]([C:5]1[C:10]([NH:11][C:12]([C:14]2[C:15](=[O:29])[N:16]([CH2:25][CH2:26][CH2:27][CH3:28])[C:17]3[C:22]([C:23]=2[OH:24])=[CH:21][CH:20]=[CH:19][CH: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][CH: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:29])[CH2:26][CH2:27][CH3:28]

Participants

3

Reactant 2

HCID 67063612N-[2-(aminosulfonyl)-4-bromophenyl]-1-benzyl-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamideHCID 67063642N-[2-(aminosulfonyl)pyridin-3-yl]-1-butyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamide

Product 1

HCID 1355253271-butyl-3-(1,1-dioxido-4H-pyrido[3,2-e][1,2,4]thiadiazin-3-yl)-4-hydroxy-2(1H)-quinolinone

Procedure

The title compound was prepared according to the procedure of Example 84D substituting the product of Example 98C for the product of Example 84C .as a white solid (0.065 g, 22%). MS (ESI−) m/z 397 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 0.96 (t, J=7.35 Hz, 3H), 1.46 (m, 2H), 1.66 (m, 2H), 4.34 (m, 2H), 7.46 (t, J=7.54 Hz, 1H), 7.82 (m, 3H), 8.23 (d, J=6.99 Hz, 1H), 8.26 (d, J=7.72 Hz, 1H), 8.70 (d, J=3.68 Hz, 1H), 14.38 (s, 1H), 15.12 (s, 1H).

Sources & evidence

ORD record
ord-cc0ebfa7d2d14041826255dd81d70e7d
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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