Acetic Acid → 4-{3-[(4-Carbamimidoylphenylamino)-(5-fluoro-8-methoxychroman-6-yl)methyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}thiazole-5-carboxylic acid trifluoroacetate

HRID 1161557Notes

Reaction equation

HRID 1161557 reaction equation
CO.C([O:5][C:6]([C:8]1[S:12][CH:11]=[N:10][C:9]=1[N:13]1[C:17](=[O:18])[NH:16][C:15]([CH:19]([C:36]2[C:37]([F:48])=[C:38]3[C:43](=[C:44]([O:46][CH3:47])[CH:45]=2)[O:42][CH2:41][CH2:40][CH2:39]3)[NH:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[N:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[O:29][N:28]=3)=[CH:23][CH:22]=2)=[N:14]1)=[O:7])C.[OH-].[Na+].C(O)(=[O:53])C>[Fe].O>[F:33][C:32]([F:35])([F:34])[C:30]([OH:53])=[O:29].[C:27]([C:24]1[CH:25]=[CH:26][C:21]([NH:20][CH:19]([C:36]2[C:37]([F:48])=[C:38]3[C:43](=[C:44]([O:46][CH3:47])[CH:45]=2)[O:42][CH2:41][CH2:40][CH2:39]3)[C:15]2[NH:16][C:17](=[O:18])[N:13]([C:9]3[N:10]=[CH:11][S:12][C:8]=3[C:6]([OH:7])=[O:5])[N:14]=2)=[CH:22][CH:23]=1)(=[NH:28])[NH2:31]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 1359821184-(3-{(5-Fluoro-8-methoxychroman-6-yl)-[4-(5-trifluoromethyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 1363892774-{3-[(4-Carbamimidoylphenylamino)-(5-fluoro-8-methoxychroman-6-yl)methyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}thiazole-5-carboxylic acid trifluoroacetate

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

To 2 ml of a methanol solution containing 74 mg of 4-(3-{(5-fluoro-8-methoxychroman-6-yl)-[4-(5-trifluoromethyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)thiazole-5-carboxylic acid ethyl ester, 0.5 ml of a 5 N sodium hydroxide aqueous solution was added. The resulting mixture was stirred at room temperature for 18 hours, and then 2 ml of acetic acid, 1.5 ml of water, and 74 mg of iron powder were added thereto. The mixture was stirred at 60° C. for 15 hours under a nitrogen atmosphere. The reaction mixture was filtered and purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% trifluoroacetic acid) to give the title compound (34 mg).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at 60° C. for 15 hours under a nitrogen atmosphere
  3. filtrationThe reaction mixture was filtered
  4. custompurified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-006c2cc437944bbc87c5f497f488fb29
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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