N-[2-(aminosulfonyl)-4-bromophenyl]-1-benzyl-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamide → HCID 135474739, compound

HRID 601175Notes

Reaction equation

HRID 601175 reaction equation
[NH2:1][S:2]([C:5]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:7]([CH3:13])[C:6]=1[NH:14][C:15]([C:17]1[C:18](=[O:35])[N:19]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:20]2[C:25]([C:26]=1[OH:27])=[CH:24][CH:23]=[CH:22][N:21]=2)=O)(=[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>Cl>[CH2:28]([N:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][N:21]=2)[C:26]([OH:27])=[C:17]([C:15]2[NH:14][C:6]3[C:7]([CH3:13])=[CH:8][CH:9]=[C:10]([O:11][CH3:12])[C:5]=3[S:2](=[O:3])(=[O:4])[N:1]=2)[C:18]1=[O:35])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 67063612N-[2-(aminosulfonyl)-4-bromophenyl]-1-benzyl-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamideHCID 67063696HCID 67063696, compound

Product 1

HCID 135474739HCID 135474739, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The title compound was prepared according to the procedure of Example 84D substituting the product of Example 209B for the product of Example 84C. The solution was then acidified with 6N aqueous HCl (10 mL), filtered and the solid washed with methanol (10 mL) to give the title compound as a white solid, (0.12 g, 56% yield). MS (ESI−) m/z 477 (M−H)+. The sodium salt of the title compound was prepared according to the procedure of Example 1D. 1H NMR (300 MHz, DMSO-d6) δ 2.37 (s, 3 H) 3.83 (s, 3 H) 5.52 (s, 2 H) 6.76 (d, J=8.5 Hz, 1 H) 7.16 (m, 2 H) 7.23 (m, 4 H) 7.37 (d, J=8.9 Hz, 1 H) 8.45 (m, 2 H), 15.67 (s, 1 H).

Workup

  1. customThe title compound was prepared
  2. filtrationfiltered
  3. washthe solid washed with methanol (10 mL)

Sources & evidence

ORD record
ord-61079191a6d64a2c907c6d92c9d61dd4
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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