Methanol → HCID 178493538, compound

HRID 1157957Notes

Reaction equation

HRID 1157957 reaction equation
C[O:2][C:3]([C:5]1[S:9][CH:8]=[N:7][C:6]=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]([O: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.[OH-].[Na+]>C(O)(=O)C>[F:29][C:18]1[C:19]([O:25][CH2:26][CH2:27][OH:28])=[CH:20][C:21]([O:23][CH3:24])=[CH:22][C:17]=1[CH:16]([NH:30][C:31]1[CH:32]=[C:33]2[C:34](=[CH:35][CH:36]=1)[C:37](=[NH:38])[NH:40][CH2:39]2)[C:12]1[NH:13][C:14](=[O:15])[N:10]([C:6]2[N:7]=[CH:8][S:9][C:5]=2[C:3]([OH:2])=[O:4])[N:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 136011093HCID 136011093, compound

Product 1

HCID 178493538HCID 178493538, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 4-(3-{[3-(t-butoxycarbonylaminomethyl)-4-cyanophenylamino]-[2-fluoro-5-methoxy-3-(2-hydroxyethoxy)phenyl]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)thiazole-5-carboxylic acid methyl ester (31 mg) and methanol (2.0 mL) there was added a 5N sodium hydroxide aqueous solution (28 μL), and the mixture was stirred overnight at room temperature. After neutralizing the mixture with acetic acid, the solvent in the mixture was distilled off under reduced pressure. Dichloromethane (2.0 mL) was added to the residue, and then a 4N hydrogen chloride-ethyl acetate solution (500 μL) was added to the mixture prior to stirring at room temperature for 15 minutes. Toluene (10 mL) was added to the mixture, and the solvent in the mixture was distilled off. The residue was purified by reverse-phase high performance liquid chromatography (acetonitrile/water mixed solvent, 0.1% acetic acid) to obtain the target compound (10 mg).

Workup

  1. distillationthe solvent in the mixture was distilled off under reduced pressure
  2. additionDichloromethane (2.0 mL) was added to the residue
  3. additiona 4N hydrogen chloride-ethyl acetate solution (500 μL) was added to the mixture
  4. stirringto stirring at room temperature for 15 minutes
  5. additionToluene (10 mL) was added to the mixture
  6. distillationthe solvent in the mixture was distilled off
  7. customThe residue was purified by reverse-phase high performance liquid chromatography (acetonitrile/water mixed solvent, 0.1% acetic acid)

Sources & evidence

ORD record
ord-26b26861211848d388cb50839fe21af8
Source dataset
uspto-grants-2010_10
Patent number
US07807690B2

Reaction notes

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