Methanol → 2-(2-Benzo[1,3]dioxol-5-yl-acetylamino)-6-fluoro-4-(4-methyl-piperazin-1-yl)-benzoic acid

HRID 2039548Notes

Reaction equation

HRID 2039548 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[C:9]([F:10])=[CH:8][C:7]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)=[CH:6][C:5]=1[NH:18][C:19](=[O:30])[CH2:20][C:21]1[CH:29]=[CH:28][C:24]2[O:25][CH2:26][O:27][C:23]=2[CH:22]=1.CO.O.[OH-].[Li+]>O1CCCC1>[O:25]1[C:24]2[CH:28]=[CH:29][C:21]([CH2:20][C:19]([NH:18][C:5]3[CH:6]=[C:7]([N:11]4[CH2:12][CH2:13][N:14]([CH3:17])[CH2:15][CH2:16]4)[CH:8]=[C:9]([F:10])[C:4]=3[C:3]([OH:31])=[O:2])=[O:30])=[CH:22][C:23]=2[O:27][CH2:26]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 670428092-(2-Benzo[1,3]dioxol-5-yl-acetylamino)-6-fluoro-4-(4-methyl-piperazin-1-yl)-benzoic acid methyl ester

Product 1

HCID 670427932-(2-Benzo[1,3]dioxol-5-yl-acetylamino)-6-fluoro-4-(4-methyl-piperazin-1-yl)-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-(2-benzo[1,3]dioxol-5-yl-acetylamino)-6-fluoro-4-(4-methyl-piperazin-1-yl)-benzoic acid methyl ester (0.15 g, 0.35 mmol) in a mixture of tetrahydrofuran (10 mL), methanol (1 mL) and water (2 mL), was added lithium hydroxide (0.15 g, 3.49 mmol). The reaction was stirred at room temperature overnight then the solvent was evaporated. The residue was diluted with water and 2 N HCl solution was added until pH 7. The solid precipitated was filtered and washed with water to obtain the 2-(2-benzo[1,3]dioxol-5-yl-acetylamino)-6-fluoro-4-(4-methyl-piperazin-1-yl)-benzoic acid crude. 2-(2-Benzo[1,3]dioxol-5-yl-acetylamino)-6-fluoro-4-(4-methyl-piperazin-1-yl)-benzoic acid was suspended in acetic anhydride (3 mL) and the reaction mixture was heated under microwave condition at 130° C. for 10 minutes. The solvent was evaporated to obtain the 2-benzo[1,3]dioxol-5-ylmethyl-5-fluoro-7-(4-methyl-piperazin-1-yl)-benzo[d][1,3]oxazin-4-one crude. To a solution of 2-benzo[1,3]dioxol-5-ylmethyl-5-fluoro-7-(4-methyl-piperazin-1-yl)-benzo[d][1,3]oxazin-4-one in dry pyridine (3 mL) was added aminoguanidine hydrogencarbonate (0.05 g, 0.39 mmol) and the mixture was heated under microwave condition at 180° C. for 15 minutes. The reaction was cooled at room temperature and diluted with water to induce the precipitation of a brown solid which was washed with a mixture MeOH/H2O 8/2, to afford the title compound (0.07 g, 46% yield).

Workup

  1. customthe solvent was evaporated
  2. additionThe residue was diluted with water and 2 N HCl solution
  3. additionwas added until pH 7
  4. customThe solid precipitated
  5. filtrationwas filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-720ef36f94ea47e097bbc5e22b26ec8d
Source dataset
uspto-grants-2013_11
Patent number
US08580783B2

Reaction notes

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