N-[2-(aminosulfonyl)-4-bromophenyl]-1-benzyl-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamide → 3-(1,1-dioxido-4H-pyrido[3,2-e][1,2,4]thiadiazin-3-yl)-4-hydroxy-1-[(2-methyl-1,3-thiazol-5-yl)methyl]-2(1H)-quinolinone

HRID 601135Notes

Reaction equation

HRID 601135 reaction equation
[NH2:1][S:2]([C:5]1[C:10]([NH:11][C:12]([CH:14]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:25][C:26]3[S:30][C:29]([CH3:31])=[N:28][CH:27]=3)[C:15]2=[O:32])=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>>[O:3]=[S:2]1(=[O:4])[C:5]2[N:6]=[CH:7][CH:8]=[CH:9][C:10]=2[NH:11][C:12]([C:14]2[C:15](=[O:32])[N:16]([CH2:25][C:26]3[S:30][C:29]([CH3:31])=[N:28][CH:27]=3)[C:17]3[C:22]([C:23]=2[OH:24])=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:1]1

Participants

3

Reactant 2

HCID 67063612N-[2-(aminosulfonyl)-4-bromophenyl]-1-benzyl-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamideHCID 67063944N-[2-(aminosulfonyl)pyridin-3-yl]-1-[(2-methyl-1,3-thiazol-5-yl)methyl]-2,4-dioxo-1,2,3,4-tetrahydroquinoline-3-carboxamide

Product 1

HCID 1354575523-(1,1-dioxido-4H-pyrido[3,2-e][1,2,4]thiadiazin-3-yl)-4-hydroxy-1-[(2-methyl-1,3-thiazol-5-yl)methyl]-2(1H)-quinolinone

Procedure

The title compound was prepared according to the procedure of Example 84D substituting the product of Example 103C for the product of Example 84C (0.033 g, 68%). MS (APCI) m/z 454 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ 2.56 (s, 3H), 5.74 (s, 2H), 7.48 (t, J=6.80 Hz, 1H), 7.82 (s, 1H), 7.88 (m, 4H), 8.24 (m, 2H), 8.71 (dd, J=4.41, 1.47 Hz, 1H), 14.01 (s, 1H).

Sources & evidence

ORD record
ord-9c66b7676bc640f19a0e785e175b6464
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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