Lithium Hydroxide → 3-Amino-6-[4-[(4-methyl-1-piperazinyl)sulfonyl]phenyl]-2-pyrazinecarboxylic acid

HRID 736606Notes

Reaction equation

HRID 736606 reaction equation
[NH2:1][C:2]1[C:3]([C:24]([O:26]C)=[O:25])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][N:7]=1.[OH-].[Li+]>O1CCCC1.O>[NH2:1][C:2]1[C:3]([C:24]([OH:26])=[O:25])=[N:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([S:14]([N:17]3[CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH2:22]3)(=[O:16])=[O:15])=[CH:12][CH:13]=2)=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68531416Methyl 3-amino-6-(4-(4-methylpiperazin-1-ylsulfonyl)phenyl)pyrazine-2-carboxylate

Product 1

HCID 685325113-Amino-6-[4-[(4-methyl-1-piperazinyl)sulfonyl]phenyl]-2-pyrazinecarboxylic acidYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 3-amino-6-[4-[(4-methyl-1-piperazinyl)sulfonyl]phenyl]pyrazine-2-carboxylate was dissolved in anhydrous tetrahydrofuran (10 mL). Lithium hydroxide (0.113 g, 4.72 mmol) in water (19 mL) was added at room temperature and the resulting mixture was stirred at 50° C. for 3 h. The tetrahydrofuran was evaporated and the pH of the water phase was adjusted to 6 with HCl (aq). The precipitated product was filtered and washed with water and dried to give 0.763 g (86% yield) of the title compound as a pale yellow solid: 1HNMR (TFA) δ 8.83 (s, 2H), 8.23 (m, 2H), 7.97 (m, 2H), 4.09 (m, 2H), 3.76 (m, 2H), 2.25 (m, 2H), 3.04 (m, 5H); 13CNMR (TFA) δ 165.81, 147.39, 139.5, 139.2, 135.7, 132.1, 131.1, 128.5, 127.3, 53.9, 43.5, 43.2; MS (ESP) m/z 378 (M++1).

Workup

  1. customThe tetrahydrofuran was evaporated
  2. filtrationThe precipitated product was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-a517e38308c14cb59aa1f6203e6514b3
Source dataset
uspto-grants-2009_09
Patent number
US07595319B2

Reaction notes

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