Hydrochloric Acid → 5-{5-Amino-6-[(methylamino)carbonyl]pyrazin-2-yl}-2-chlorobenzoic acid

HRID 646692Notes

Reaction equation

HRID 646692 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:12]2[CH:13]=[CH:14][C:15]([Cl:22])=[C:16]([CH:21]=2)[C:17]([O:19]C)=[O:18])=[N:6][C:7]=1[C:8]([NH:10][CH3:11])=[O:9].[OH-].[Na+].Cl>CO.O1CCCC1.C(OCC)(=O)C>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:12]2[CH:13]=[CH:14][C:15]([Cl:22])=[C:16]([CH:21]=2)[C:17]([OH:19])=[O:18])=[N:6][C:7]=1[C:8]([NH:10][CH3:11])=[O:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68651344Methyl 5-{5-amino-6-[(methylamino)carbonyl]pyrazin-2-yl}-2-chlorobenzoate

Product 1

HCID 686515865-{5-Amino-6-[(methylamino)carbonyl]pyrazin-2-yl}-2-chlorobenzoic acidYield 48%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl 5-{5-amino-6-[(methylamino)carbonyl]pyrazin-2-yl}-2-chlorobenzoate (96 mg, 31 mmol) in methanol/tetrahydrofuran (1:1, 5.0 mL) was added 2.0 N aqueous sodium hydroxide (0.16 g, 4.00 mmol). The reaction was stirred overnight at room temperature. Reaction was neutralized with 2.0 N aqueous hydrochloric acid (4 mL) and diluted with ethyl acetate (100 mL). The organic layer was washed with water (20 mL), saturated aqueous sodium chloride (30 mL), dried over magnesium sulfate, filtered, and concentrated to afford 5-{5-amino-6-[(methylamino)carbonyl]pyrazin-2-yl}-2-chlorobenzoic acid (45 mg, 48% yield). 1H NMR (400 MHz, d6-DMSO): 13.42 (br s, 1H), 8.90 (br s, 1H), 8.45 (d, 1H), 8.32 (dd, 1H), 7.85 (br s, 2H), 7.60 (d, 2H), 2.82 (s, 3H); MS (EI) for C13H11N4O3Cl: 307 (MH+).

Workup

  1. customReaction
  2. washThe organic layer was washed with water (20 mL), saturated aqueous sodium chloride (30 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4f76689bc72f4beb8ea9b8b19930a429
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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