Water → HCID 22046447, compound

HRID 1830715Notes

Reaction equation

HRID 1830715 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[N:18][CH:17]=[CH:16][N:15]=2)=[O:12])=[C:6]([O:20][CH3:21])[CH:5]=1.O.O.[OH-].[Li+]>CO>[CH3:21][O:20][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[NH:10][C:11]([NH:13][C:14]1[CH:19]=[N:18][CH:17]=[CH:16][N:15]=1)=[O:12])[C:3]([OH:22])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67254548HCID 67254548, compound

Product 1

HCID 22046447HCID 22046447, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
65 °C

Procedure

To a stirred suspension of 3-methoxy-4-(3-pyrazin-2-yl-ureido)-benzoic acid methyl ester (6.07 g, 20 mmol) in 200 mL 3:1 MeOH:H2O at room temperature under nitrogen was added lithium hydroxide monohydrate (8.4 g, 200 mmol) and the reaction heated to 65 ° C. overnight. The reaction was then cooled to room temperature and most of the methanol removed by rotary evaporation. The remaining suspension was neutralized to pH about 4 with concentrated HCl. The formed precipitate was isolated by filtration and rinsing with H2O and then drying under high vacuum to give the desired acid as a white solid (5.34 g, 93%). 1H-NMR (400 MHz, d6-DMSO) δ 8.89 (br s, 1H), 8.34 (s, 1H), 8.24 (s, 1H), 8.16 (d, 1H), 8.16 (d, 1H), 7.56 (s, 1H), 7.50 (d, 1H), 3.91 (s, 3H)

Workup

  1. customremoved by rotary evaporation
  2. customThe formed precipitate was isolated by filtration
  3. washrinsing with H2O
  4. customdrying under high vacuum

Sources & evidence

ORD record
ord-ab28baaa251a4ca3ad247513b5c4d0d1
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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