Trifluoroacetic acid → 6-[(2-Aminoethyl)amino]nicotinonitrile trifluoroacetate

HRID 2171483Notes

Reaction equation

HRID 2171483 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][CH2:10][CH2:11][NH:12]C(=O)OC(C)(C)C)=[N:7][CH:8]=1)#[N:2].[F:20][C:21]([F:26])([F:25])[C:22]([OH:24])=[O:23]>ClCCl>[F:20][C:21]([F:26])([F:25])[C:22]([OH:24])=[O:23].[NH2:12][CH2:11][CH2:10][NH:9][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 47453716tert-Butyl (2-((5-cyanopyridin-2-yl)amino)ethyl)carbamate

Product 1

HCID 687096656-[(2-Aminoethyl)amino]nicotinonitrile trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.0 g (15.25 mmol) of tert-butyl {2-[(5-cyanopyridin-2-yl)amino]ethyl}carbamate (Example 12A) are dissolved in 150 ml of dichloromethane, and 17.39 g (152.5 mmol) of trifluoroacetic acid are slowly injected. The mixture is stirred at RT for 16 h and then all volatile constituents are removed in vacuo. 4.3 g (91% of theory) of the product are obtained as a resin.

Workup

  1. customall volatile constituents are removed in vacuo
  2. custom4.3 g (91% of theory) of the product are obtained as a resin

Sources & evidence

ORD record
ord-3af1babd167b4fb296e2a0bca87e0642
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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