Methanol → HCID 178492110, compound

HRID 1157947Notes

Reaction equation

HRID 1157947 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[C:18]([F:29])=[C:19]3[C:24](=[C:25]([O:27][CH3:28])[CH:26]=2)[O:23][CH2:22][CH2:21][CH2:20]3)=[N:11]1)=[O:4].CO.[OH-].[Na+]>C(O)(=O)C>[F:29][C:18]1[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:6]3[N:7]=[CH:8][S:9][C:5]=3[C:3]([OH:2])=[O:4])[N:11]=2)=[CH:26][C:25]([O:27][CH3:28])=[C:24]2[C:19]=1[CH2:20][CH2:21][CH2:22][O:23]2

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 135999748HCID 135999748, compound

Product 1

HCID 178492110HCID 178492110, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 4-(3-{[3-(t-butoxycarbonylaminomethyl)-4-cyanophenylamino]-(5-fluoro-8-methoxychroman-6-yl)methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)thiazole-5-carboxylic acid methyl ester (74 mg) and methanol (2.0 mL) there was added aqueous 5N sodium hydroxide (111 μL), and the mixture was stirred at room temperature for 3 hours and 15 minutes. After adding acetic acid (52 μL) to the mixture, the solvent in the mixture was distilled off under reduced pressure. Dichloromethane (2.0 mL) was added to the residue, TFA (400 μL) was added to the resulting solution and the mixture was stirred at room temperature for 5 hours. Dichloromethane (50 mL) was added to the mixture, which was then stirred at room temperature for 14 hours. 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 (21 mg).

Workup

  1. distillationthe solvent in the mixture was distilled off under reduced pressure
  2. additionDichloromethane (2.0 mL) was added to the residue, TFA (400 μL)
  3. additionwas added to the resulting solution
  4. stirringthe mixture was stirred at room temperature for 5 hours
  5. additionDichloromethane (50 mL) was added to the mixture, which
  6. stirringwas then stirred at room temperature for 14 hours
  7. additionToluene (10 mL) was added to the mixture
  8. distillationthe solvent in the mixture was distilled off
  9. customThe residue was purified by reverse-phase high performance liquid chromatography (acetonitrile/water mixed solvent, 0.1% acetic acid)

Sources & evidence

ORD record
ord-cb20c32dd1584843b7e49f4620e1fba5
Source dataset
uspto-grants-2010_10
Patent number
US07807690B2

Reaction notes

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