Sodium Hydroxide → HCID 178436897, compound

HRID 1157969Notes

Reaction equation

HRID 1157969 reaction equation
C[O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[N:10]1[C:14](=[O:15])[NH:13][C:12]([CH:16]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[C:33]([CH2:39][NH:40]C(OC(C)(C)C)=O)[CH:32]=2)[C:17]2[CH:22]=[C:21]([CH2:23][CH3:24])[CH:20]=[C:19]([O:25][CH2:26][CH2:27][OH:28])[C:18]=2[F:29])=[N:11]1)=[O:4].CO.C1COCC1.[OH-].[Na+]>C(O)(=O)C>[CH2:23]([C:21]1[CH:20]=[C:19]([O:25][CH2:26][CH2:27][OH:28])[C:18]([F:29])=[C:17]([CH:16]([NH:30][C:31]2[CH:32]=[C:33]3[C:34](=[CH:35][CH:36]=2)[C:37](=[NH:38])[NH:40][CH2:39]3)[C:12]2[NH:13][C:14](=[O:15])[N:10]([C:9]3[CH:8]=[CH:7][S:6][C:5]=3[C:3]([OH:2])=[O:4])[N:11]=2)[CH:22]=1)[CH3:24]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 135999745HCID 135999745, compound

Product 1

HCID 178436897HCID 178436897, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-(3-{[3-(t-butoxycarbonylaminomethyl)-4-cyanophenylamino]-[5-ethyl-2-fluoro-3-(2-hydroxyethoxy)phenyl]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)thiophene-2-carboxylic acid methyl ester (31 mg), a methanol:THF (2:1) mixed solvent (1.5 mL) and a 5N sodium hydroxide aqueous solution (0.1 mL) was heated for 14 hours at 65° C. under a nitrogen atmosphere. Acetic acid was added to the mixture, which was then purified by reverse-phase high performance liquid chromatography (acetonitrile/water mixed solvent, 0.1% acetic acid) to obtain the target compound (9.0 mg).

Workup

  1. customwas then purified by reverse-phase high performance liquid chromatography (acetonitrile/water mixed solvent, 0.1% acetic acid)

Sources & evidence

ORD record
ord-0c167e2d9edd40ed9ed8c621991f8576
Source dataset
uspto-grants-2010_10
Patent number
US07807690B2

Reaction notes

Loading…