Hydrochloric Acid → (RS)-N-(4-carbamimidoyl-benzyl)-2-(2,6-difluoro-3-hydroxy-phenyl)-2-ethoxy-acetamide hydrochloride

HRID 1247384Notes

Reaction equation

HRID 1247384 reaction equation
C(OC(=O)[NH:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][NH:20][C:21](=[O:35])[CH:22]([C:26]2[C:31]([F:32])=[CH:30][CH:29]=[C:28]([OH:33])[C:27]=2[F:34])[O:23][CH2:24][CH3:25])=[CH:15][CH:14]=1)=[NH:12])C1C=CC=CC=1.[ClH:37]>CCO.[Pd]>[ClH:37].[C:11]([C:13]1[CH:14]=[CH:15][C:16]([CH2:19][NH:20][C:21](=[O:35])[CH:22]([C:26]2[C:31]([F:32])=[CH:30][CH:29]=[C:28]([OH:33])[C:27]=2[F:34])[O:23][CH2:24][CH3:25])=[CH:17][CH:18]=1)(=[NH:10])[NH2:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 140474512benzyl N-[4-[[[2-(2,6-difluoro-3-hydroxyphenyl)-2-ethoxyacetyl]amino]methyl]benzenecarboximidoyl]carbamate

Product 1

HCID 21905430(RS)-N-(4-carbamimidoyl-benzyl)-2-(2,6-difluoro-3-hydroxy-phenyl)-2-ethoxy-acetamide hydrochlorideYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

(RS)-[(4-{[2-(2,6-Difluoro-3-hydroxy-phenyl)-2-ethoxy-acetylamino]-methyl}-phenyl)-imino-methyl]-carbamic acid benzyl ester (250 mg) was dissolved in EtOH (20 ml) and 0.9 N HCl in EtOH (5 ml) was added. After 10 min stirring 10% Pd/C (11 mg) was added and the mixture was hydrogenated 2 h at rt under 1 atm H2. Filtration, evaporation of the solvent and trituration with MeCN (4 ml) afforded the solid product that was washed with two portions of Et2O (5 ml). After drying on the vacuum at 50° C. 175 mg (87%) of (RS)-N-(4-carbamimidoyl-benzyl)-2-(2,6-difluoro-3-hydroxy-phenyl)-2-ethoxy-acetamide hydrochloride were obtained. White solid. MS 364.0 ([M+H]+).

Workup

  1. additionwas added
  2. filtrationFiltration, evaporation of the solvent and trituration with MeCN (4 ml)
  3. customafforded the solid product that
  4. washwas washed with two portions of Et2O (5 ml)
  5. customAfter drying on the vacuum at 50° C

Sources & evidence

ORD record
ord-aeb32a17f4794ab589d6ad179bdcf7ed
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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