HCID 86600900, compound → HCID 68904676, compound

HRID 2110350Notes

Reaction equation

HRID 2110350 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][N:8]([C@@H:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C@H:12]([OH:16])[CH2:13][NH:14][CH3:15])[C:7]=12.[H][H]>C(O)C.[Pd]>[ClH:1].[ClH:1].[CH3:15][NH:14][CH2:13][C@@H:12]([OH:16])[C@H:11]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[N:8]1[C:7]2=[CH:2][N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9]1

Participants

5

Reactant 2

HCID 86600900HCID 86600900, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68904676HCID 68904676, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(1S,2R)-1-(7-chloro-pyrrolo[2,3-c]pyridine-1-yl)-3-methylamino-1-phenyl-propan-2-ol (0.12 g, 0.38 mmol) was dissolved in ethanol (20 mL) and treated with 10% palladium on carbon. The reaction mixture placed under 50 psi of hydrogen on a Parr shaker for 15 hours. The reaction mixture was filtered through a Celite pad and the filtrate was concentrated in vacuo. The crude product was purified via Biotage Horizon (Flash 25 S, silica, gradient from 30% to 100% of 0.9% ammonium hydroxide in 10% methanol-methylene chloride/methylene chloride) to give a white solid as the free base of the expected product. The free base was dissolved in a minimum amount of ethanol and treated with a 1 N ethereal solution of hydrochloric acid until the solution was pH=3 followed by diethyl ether. The product was then crystallized by adding a minimum amount of ethyl acetate to afford the titled compound, (1S,2R)-3-methylamino-1-phenyl-1-(1H-pyrrolo[2,3-c]pyrid in-1-yl)-propan-2-ol dihydrochloride as a white solid. MS (ES) m/z 282.1.

Workup

  1. filtrationThe reaction mixture was filtered through a Celite pad
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe crude product was purified via Biotage Horizon (Flash 25 S, silica, gradient from 30% to 100% of 0.9% ammonium hydroxide in 10% methanol-methylene chloride/methylene chloride)

Sources & evidence

ORD record
ord-c252c08764134ab48fc5df85ce7da319
Source dataset
uspto-grants-2009_04
Patent number
US07517899B2

Reaction notes

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