Hydrochloric Acid → HCID 67517721, compound

HRID 2173356Notes

Reaction equation

HRID 2173356 reaction equation
C([N:8]1[CH2:14][CH:13]2[N:15]([C:16](=[O:29])[CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N:24]4[CH:28]=[N:27][N:26]=[N:25]4)=[CH:20][CH:19]=3)[CH:10]([CH2:11][CH2:12]2)[CH2:9]1)C1C=CC=CC=1.Cl>C(O)C.[Pd]>[CH:13]12[N:15]([C:16](=[O:29])[CH2:17][C:18]3[CH:19]=[CH:20][C:21]([N:24]4[CH:28]=[N:27][N:26]=[N:25]4)=[CH:22][CH:23]=3)[CH:10]([CH2:11][CH2:12]1)[CH2:9][NH:8][CH2:14]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67517732HCID 67517732, compound

Product 1

HCID 67517721HCID 67517721, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-(3-Benzyl-3,8-diazabicyclo[3.2.1]oct-8-yl)-2-[4-(1H-tetrazol-1-yl)phenyl]ethanone (580 mg, 1.49 mmol) was dissolved in ethanol (20 mL), concentrated HCl solution was added (37%, 2.0 mL, 24.4 mmol), followed by palladium on carbon (200 mg). The mixture was degassed and stirred under hydrogen gas at room temperature overnight. The reaction mixture was filtered through a Celite® plug and the filtrate was concentrated. The product was partitioned between DCM and saturated sodium bicarbonate solution, then the organic layer was dried over MgSO4. Purification by MPLC eluting with 10% methanol in DCM afforded the title compound. LC/MS: [(M+1)]+=299.

Workup

  1. customThe mixture was degassed
  2. filtrationThe reaction mixture was filtered through a Celite® plug
  3. concentrationthe filtrate was concentrated
  4. customThe product was partitioned between DCM and saturated sodium bicarbonate solution
  5. dry with materialthe organic layer was dried over MgSO4
  6. customPurification by MPLC
  7. washeluting with 10% methanol in DCM

Sources & evidence

ORD record
ord-b6a0d28811a24f6591c362974f81490f
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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