Hydrochloric Acid → Hydrochloric Acid

HRID 511119Notes

Reaction equation

HRID 511119 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22]2[CH:27]=[C:26]([CH3:28])[C:25]([N+:29]([O-:31])=[O:30])=[CH:24][N:23]=2)[CH2:17][CH2:16]1)=O)(C)(C)C.[ClH:32]>ClCCl.O1CCOCC1>[ClH:32].[CH3:28][C:26]1[C:25]([N+:29]([O-:31])=[O:30])=[CH:24][N:23]=[C:22]([NH:21][CH:18]2[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]2)[CH:27]=1.[ClH:32]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 58577103HCID 58577103, compound

Product 2

HCID 313Hydrochloric AcidHCID 66671832HCID 66671832, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

Trifluoroacetic acid (1 mL) is added to a solution of 4-(4-methyl-5-nitro-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (170 mg; 0.51 mmol, prepared in accordance with Example 69) in dichloromethane (5 mL) under stiffing and the resulting mixture is stirred for 30 minutes at room temperature. The mixture is then concentrated under reduced pressure and co-evaporated with dichloromethane (2×10 mL). The residue obtained is diluted in dioxane (3 mL) and a 4N solution of hydrochloric acid in dioxane (3 mL) is added. The precipitate formed is filtered and is triturated with a small volume of acetone and dried under high vacuum to afford the desired product as hydrochloride (120 mg; 0.44 mmol).

Workup

  1. concentrationThe mixture is then concentrated under reduced pressure and co-evaporated with dichloromethane (2×10 mL)
  2. customThe residue obtained
  3. customThe precipitate formed
  4. filtrationis filtered
  5. customis triturated with a small volume of acetone
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-dfffe64f971a40e198304d8be89229b0
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

Loading…