Hydrochloric Acid → HCID 42639651, compound

HRID 2220423Notes

Reaction equation

HRID 2220423 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C@@H:8]([OH:43])[CH2:9][N:10]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([NH:34][S:35]([CH3:38])(=[O:37])=[O:36])=[O:33])=[C:28]([CH2:39][CH:40]([CH3:42])[CH3:41])[CH:27]=3)=[CH:22][CH:21]=2)C(=O)OC(C)(C)C)=[CH:4][CH:3]=1.C([O-])=O.[NH4+].[ClH:48]>[Pd].CO.O.C(OCC)(=O)C>[ClH:1].[ClH:48].[OH:43][C@H:8]([C:5]1[CH:6]=[N:7][CH:2]=[CH:3][CH:4]=1)[CH2:9][NH:10][CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([NH:34][S:35]([CH3:38])(=[O:36])=[O:37])=[O:33])=[C:28]([CH2:39][CH:40]([CH3:42])[CH3:41])[CH:27]=2)=[CH:24][CH:25]=1

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 2723923Ammonium formateHCID 86598955HCID 86598955, compound

Product 1

HCID 42639651HCID 42639651, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

The mixture of tert-butyl [(2R)-2-(6-chloro-3-pyridyl)-2-hydroxyethyl][2-[3′-isobutyl-4′-[[(methylsulfonyl)amino]-carbonyl]-4-biphenylyl]ethyl]carbamate (310 mg), ammonium formate (155 mg) and palladium on carbon powder (155 mg) in methanol (5 ml) and water (0.5 ml) was refluxed for 30 minutes. The catalyst was filtered off, and the filtrate was poured into water and extracted with chloroform-methanol (19:1). The organic layer was washed with brine, dried over magnesium sulfate, and evaporated to give pyridine product. To a solution of the product in ethyl acetate (1.8 ml) was added 4N hydrogen chloride in ethyl acetate (1.8 ml), and the mixture was stirred at room temperature for 16 hours. The resultant solid was collected by filtration and dried to give 4′-[2-[[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]amino]-ethyl]-3-isobutyl-N-(methylsulfonyl)-4-biphenylcarboxamide dihydrochloride (93 mg).

Workup

  1. temperaturewas refluxed for 30 minutes
  2. filtrationThe catalyst was filtered off
  3. additionthe filtrate was poured into water
  4. extractionextracted with chloroform-methanol (19:1)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customto give pyridine product
  9. filtrationThe resultant solid was collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-902f38f9e7da4987a29023e432b1afae
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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