Sodium Hydroxide → (e)-6-{2-[Methyl-(3-methyl-benzo[b]thiophen-2-ylmethyl)carbamoyl]vinyl}-2-oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid sodium salt

HRID 1362310Notes

Reaction equation

HRID 1362310 reaction equation
C([O:3][C:4]([C:6]1[C:7](=[O:33])[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12](/[CH:16]=[CH:17]/[C:18](=[O:32])[N:19]([CH3:31])[CH2:20][C:21]1[S:25][C:24]3[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=3[C:22]=1[CH3:30])=[CH:11][N:10]=2)=[O:5])C.[OH-].[Na+:35]>CO.C(Cl)Cl.O>[Na+:35].[CH3:31][N:19]([CH2:20][C:21]1[S:25][C:24]2[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=2[C:22]=1[CH3:30])[C:18](/[CH:17]=[CH:16]/[C:12]1[CH:13]=[C:14]2[C:9](=[N:10][CH:11]=1)[NH:8][C:7](=[O:33])[C:6]([C:4]([O-:5])=[O:3])=[CH:15]2)=[O:32]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 59277530(E)-6-{2-[methyl-(3-methyl-benzo[b]thiophen-2-ylmethyl)carbamoyl]vinyl}-2-oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester

Product 1

HCID 23674475(e)-6-{2-[Methyl-(3-methyl-benzo[b]thiophen-2-ylmethyl)carbamoyl]vinyl}-2-oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid sodium saltYield 25%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of (E)-6-{2-[methyl-(3-methyl-benzo[b]thiophen-2-ylmethyl)carbamoyl]vinyl}-2-oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester (349 mg, 0.76 mmol) in MeOH (10 mL) and CH2Cl2 (5 mL) was added NaOH (1.53 mL of a 0.995 M solution in H2O, 1.53 mmol) dropwise. The mixture was stirred at room temperature overnight. The solid was collected by filtration and then dried under vacuum at 50° C. for 2 d. Trituration with 5:1 MeCN/H2O gave the title compound (85 mg, 25%) as an off-white solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6+TFA-d) δ 9.15 (s, 1H), 8.85 (s, 2H), 7.88 (d, J=7.5 Hz, 1H), 7.76-7.58 (m, 2H), 7.46-7.34 (m, 3H), 5.15-4.92 (m, 2H), 3.20-2.98 (m, 3H), 2.44 (s, 3H); MS (ESI) m/e 434 (M−Na+2H)+.

Workup

  1. filtrationThe solid was collected by filtration
  2. customdried under vacuum at 50° C. for 2 d

Sources & evidence

ORD record
ord-eca691155bcb466f9033748d9c16f008
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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