Methanol → HCID 22046499, compound

HRID 1830735Notes

Reaction equation

HRID 1830735 reaction equation
C[O:2][C:3](=[O:27])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([NH:12][C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([CH3:22])=[CH:18][N:17]=2)=[O:14])=[CH:6][C:5]=1[C:23]([F:26])([F:25])[F:24].CO.O.[OH-].[Li+]>O>[CH3:11][O:10][C:8]1[C:7]([NH:12][C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([CH3:22])=[CH:18][N:17]=2)=[O:14])=[CH:6][C:5]([C:23]([F:26])([F:24])[F:25])=[C:4]([CH:9]=1)[C:3]([OH:27])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 67254666HCID 67254666, compound

Product 1

HCID 22046499HCID 22046499, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred suspension of 5-methoxy-4-[3-(5-methyl-pyrazin-2-yl)-ureido]-2-trifluoromethyl-benzoic acid methyl ester (257 mg, 0.67 mmol) in 6.7 mL 3:1 MeOH:H2O at room temperature under nitrogen was added lithium hydroxide monohydrate (281 mg, 6.7 mmol) and the mixture was heated to 85° C. After stirring overnight the reaction was cooled to room temperature, MeOH was removed by rotovap and the residual suspension was neutralized with concentrated HCl to pH of approximately 5. The suspension was filtered and rinsed with H2O and the filter cake dried under high vacuum to give the acid as a white solid (161 mg, 61%). 1H-NMR (400 MHz, d6-DMSO) δ8.90 (br s, 1H), 8.63 (s, 1H), 8.22 (s, 1H), 7.38 (s, 1H), 4.00 (s, 3H), 2.42 (s, 3H). LRMS (esi, negative) m/e 369.0 (M−1).

Workup

  1. temperaturewas cooled to room temperature
  2. customMeOH was removed by rotovap
  3. filtrationThe suspension was filtered
  4. washrinsed with H2O
  5. customthe filter cake dried under high vacuum

Sources & evidence

ORD record
ord-e380ed42c81946468a9278b0b4cb512c
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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