Hydrochloric Acid → 4-{[(R)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl](5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]-triazol-3-yl)methyl]amino}benzamidine hydrochloride

HRID 2089688

Reaction equation

HRID 2089688 reaction equation
CO[C@H](C1C=CC=CC=1)C(O)=O.[F:13][C:14]1[C:19]([O:20][CH2:21][CH2:22][OH:23])=[CH:18][C:17]([O:24][CH3:25])=[CH:16][C:15]=1[C@@H:26]([NH:39][C:40]1[CH:48]=[CH:47][C:43]([C:44]([NH2:46])=[NH:45])=[CH:42][CH:41]=1)[C:27]1[NH:31][C:30](=[O:32])[N:29]([C:33]2[N:38]=[CH:37][CH:36]=[CH:35][N:34]=2)[N:28]=1.CO.[ClH:51]>C(O)C>[ClH:51].[F:13][C:14]1[C:19]([O:20][CH2:21][CH2:22][OH:23])=[CH:18][C:17]([O:24][CH3:25])=[CH:16][C:15]=1[C@@H:26]([NH:39][C:40]1[CH:41]=[CH:42][C:43]([C:44]([NH2:46])=[NH:45])=[CH:47][CH:48]=1)[C:27]1[NH:31][C:30](=[O:32])[N:29]([C:33]2[N:34]=[CH:35][CH:36]=[CH:37][N:38]=2)[N:28]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 1363340344-{[(R)-[2-fluoro-3-(2-hy droxy ethoxy)-5-methoxyphenyl] (5-oxo-1-pyrimidi n-2-yl-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]amino}benzamidine (R)-methoxyphenylacetate

Product 1

HCID 1363340354-{[(R)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl](5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]-triazol-3-yl)methyl]amino}benzamidine hydrochlorideYield 90.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 4-{[(R)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl](5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]amino}benzamidine (R)-methoxyphenylacetate (20 g, 30.2 mmol), methanol (200 mL), and ethanol (400 mL), 5 N hydrochloric acid (20 mL, 100 mmol) was added to dissolve the same. A seed crystal of the captioned compound was added to the reaction solution, and the resulting mixture was stirred overnight at room temperature. The precipitated solid was filtered and sequentially washed with a mixed solvent of ethanol and methanol (ethanol:methanol=2:1, 50 mL) and tert-butyl methyl ether (50 mL). The solid obtained was dried under air flow to obtain the captioned compound (14.52 g) as a white solid.

Workup

  1. additionwas added
  2. dissolutionto dissolve the same
  3. additionA seed crystal of the captioned compound was added to the reaction solution
  4. filtrationThe precipitated solid was filtered
  5. washsequentially washed with a mixed solvent of ethanol and methanol (ethanol:methanol=2:1, 50 mL) and tert-butyl methyl ether (50 mL)
  6. customThe solid obtained
  7. customwas dried under air flow

Sources & evidence

ORD record
ord-3f7cb31ff46c4440be0c778663882283
Source dataset
uspto-grants-2013_05
Patent number
US08436009B2

Linked notes

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