Methanol → 5-{3-[(4-carbamimidoylphenylamino)-(5-fluoro-8-methoxychroman-6-yl)methyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1161555Notes

Reaction equation

CO.O.[CH2:4]([O:6][C:7]([C:9]1[CH:10]=[N:11][NH:12][C:13]=1[N:14]1[C:18](=[O:19])[NH:17][C:16]([CH:20]([C:37]2[C:38]([F:49])=[C:39]3[C:44](=[C:45]([O:47][CH3:48])[CH:46]=2)[O:43][CH2:42][CH2:41][CH2:40]3)[NH:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[N:32]=C(C(F)(F)F)O[N:29]=3)=[CH:24][CH:23]=2)=[N:15]1)=[O:8])[CH3:5]>[Fe].C(O)(=O)C>[CH2:4]([O:6][C:7]([C:9]1[CH:10]=[N:11][NH:12][C:13]=1[N:14]1[C:18](=[O:19])[NH:17][C:16]([CH:20]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([C:28](=[NH:29])[NH2:32])=[CH:24][CH:23]=2)[C:37]2[C:38]([F:49])=[C:39]3[C:44](=[C:45]([O:47][CH3:48])[CH:46]=2)[O:43][CH2:42][CH2:41][CH2:40]3)=[N:15]1)=[O:8])[CH3:5]

Participants

Conditions

Temperature: 60 °C

Procedure

Iron powder (64 mg) was added to 6 ml of a methanol:water:acetic acid=1:1:1 mixed solvent solution containing 74 mg of 5-(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)-1H-pyrazole-4-carboxylic acid ethyl ester. The resulting mixture was stirred at 60° C. for 20 hours under a nitrogen atmosphere. After filtration, the reaction mixture was purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid) to give 22 mg of 5-{3-[(4-carbamimidoylphenylamino)-(5-fluoro-8-methoxychroman-6-yl)methyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}-1H-pyrazole-4-carboxylic acid ethyl ester.

Workup

filtrationAfter filtration
customthe reaction mixture was purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid)

Sources & evidence

ORD record: ord-ee316f387bb0478fbcdab125303253d8
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816522B2

Reaction notes

Loading…