Methanol → 3-methoxy-2,2-dimethylpropionic acid 5-[[3-(2-acetoxyethoxy)-2-fluoro-5-methoxyphenyl]-(4-carbamimidoylphen ylamino)methyl]-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester acetate

HRID 2089638

Reaction equation

HRID 2089638 reaction equation
[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:9]([F:57])=[C:10]([CH:16]([NH:39][C:40]2[CH:45]=[CH:44][C:43]([C:46]([NH2:56])=[N:47]C(=O)C3C=CC=CC=3)=[CH:42][CH:41]=2)[C:17]2[N:18]=[C:19]([O:28][CH2:29][O:30][C:31](=[O:38])[C:32]([CH3:37])([CH3:36])[CH2:33][O:34][CH3:35])[N:20]([C:22]3[N:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[N:21]=2)[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1)(=[O:3])[CH3:2].CO>C(O)(=O)C>[C:1]([OH:4])(=[O:3])[CH3:2].[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:9]([F:57])=[C:10]([CH:16]([NH:39][C:40]2[CH:45]=[CH:44][C:43]([C:46](=[NH:47])[NH2:56])=[CH:42][CH:41]=2)[C:17]2[N:18]=[C:19]([O:28][CH2:29][O:30][C:31](=[O:38])[C:32]([CH3:37])([CH3:36])[CH2:33][O:34][CH3:35])[N:20]([C:22]3[N:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[N:21]=2)[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 674705203-methoxy-2,2-dimethylpropionic acid 5-[[3-(2-acetoxyethoxy)-2-fluoro-5-methoxyphenyl]-(4-{amino[benzoylimino]methyl}phenylamino)methyl]-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester

Product 1

HCID 674699453-methoxy-2,2-dimethylpropionic acid 5-[[3-(2-acetoxyethoxy)-2-fluoro-5-methoxyphenyl]-(4-carbamimidoylphen ylamino)methyl]-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester acetateYield 168.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

Under nitrogen atmosphere, a mixture of 3-methoxy-2,2-dimethylpropionic acid 5-[[3-(2-acetoxyethoxy)-2-fluoro-5-methoxyphenyl]-(4-{amino[benzoylimino]methyl}phenylamino)methyl]-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester (184 mg), methanol (10 mL), and acetic acid (1 mL) was stirred at 40° C. for 15 hours. Under reduced pressure, the solvent in the mixture was distilled off. The residue obtained was purified by reverse phase silica gel column chromatography (mixed solvent of acetonitrile-water, containing 0.1% of acetic acid) to obtain the captioned compound (146 mg).

Workup

  1. distillationUnder reduced pressure, the solvent in the mixture was distilled off
  2. customThe residue obtained
  3. customwas purified by reverse phase silica gel column chromatography (mixed solvent of acetonitrile-water, containing 0.1% of acetic acid)

Sources & evidence

ORD record
ord-09cbbe893859437d9856ece28bb70eb6
Source dataset
uspto-grants-2013_05
Patent number
US08436009B2

Linked notes

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