Methanol → 2,2-dimethylmalonic acid 5-{(4-carbamimidoylphenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-metho xyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester 2,2-dimethylpropyl ester acetate

HRID 2089666

Reaction equation

HRID 2089666 reaction equation
[CH3:1][C:2]([CH3:59])([CH3:58])[CH2:3][O:4][C:5](=[O:57])[C:6]([CH3:56])([CH3:55])[C:7]([O:9][CH2:10][O:11][C:12]1[N:13]([C:49]2[N:54]=[CH:53][CH:52]=[CH:51][N:50]=2)[N:14]=[C:15]([CH:17]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]([NH2:48])=[N:39]C(=O)C3C=CC=CC=3)=[CH:34][CH:33]=2)[C:18]2[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH2:27][CH2:28][OH:29])[C:19]=2[F:30])[N:16]=1)=[O:8].CO>C(O)(=O)C>[C:5]([OH:57])(=[O:4])[CH3:6].[CH3:1][C:2]([CH3:59])([CH3:58])[CH2:3][O:4][C:5](=[O:57])[C:6]([CH3:56])([CH3:55])[C:7]([O:9][CH2:10][O:11][C:12]1[N:13]([C:49]2[N:50]=[CH:51][CH:52]=[CH:53][N:54]=2)[N:14]=[C:15]([CH:17]([NH:31][C:32]2[CH:33]=[CH:34][C:35]([C:38](=[NH:39])[NH2:48])=[CH:36][CH:37]=2)[C:18]2[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH2:27][CH2:28][OH:29])[C:19]=2[F:30])[N:16]=1)=[O:8]

Participants

4

Reactant 2

HCID 887MethanolHCID 682128732,2-dimethylmalonic acid 5-{(4-{amino[benzoylimino]methyl}phenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester 2,2-dimethylpropyl ester

Product 1

HCID 866773942,2-dimethylmalonic acid 5-{(4-carbamimidoylphenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-metho xyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester 2,2-dimethylpropyl ester acetateYield 181.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 2,2-dimethylmalonic acid 5-{(4-{amino[benzoylimino]methyl}phenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester 2,2-dimethylpropyl ester (500 mg) and methanol (4 mL), acetic acid (1 mL) was added, and the resulting mixture was stirred at 40° C. for 4 hours. The mixture was concentrated under reduced pressure, and 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 (430 mg).

Workup

  1. additionwas added
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue obtained
  4. 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-20b40d2bd81a4471912bb4b8601fd824
Source dataset
uspto-grants-2013_05
Patent number
US08436009B2

Linked notes

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