Trifluoroacetic acid → Ammonia

HRID 2182266Notes

Reaction equation

HRID 2182266 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]2[CH2:15][CH2:14][CH2:13][N:12](C([O:18][C:19]([CH3:22])(C)C)=O)[CH2:11][CH2:10]2)[CH:6]=[N:7][CH:8]=1)#[CH:2].F[C:24](F)(F)[C:25]([OH:27])=[O:26].[OH-:30].[Na+]>ClCCl>[NH3:7].[C:25]([OH:27])(=[O:26])/[CH:24]=[CH:22]/[C:19]([OH:18])=[O:30].[C:1]([C:3]1[CH:4]=[C:5]([N:9]2[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[N:7][CH:8]=1)#[CH:2]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 22478542HCID 22478542, compound

Product 2

HCID 222AmmoniaHCID 131724660HCID 131724660, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(5-ethynyl-3-pyridyl)-4-tert-butoxycarbonyl-homopiperazine (0.13 g, 0.43 mmol), trifluoro acetic acid (0.98 g, 8.6 mmol) and dichloromethane (10 ml) was stirred for 5 h. Aqueous sodium hydroxide (1 M, 15 ml) was added the organic phase was separated and the aqueous phase was extracted twice with dichloromethane (15 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound. The corresponding salt was obtained by addition of a diethyl ether and methanol mixture (9:1) saturated with fumaric acid. Yield 30 mg, 22%. Mp 172.5-174.0° C.

Workup

  1. customwas separated
  2. extractionthe aqueous phase was extracted twice with dichloromethane (15 ml)

Sources & evidence

ORD record
ord-0b2839a32239483c971ae87a0674431e
Source dataset
uspto-grants-2005_05
Patent number
US06897219B2

Reaction notes

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