Hydrochloric Acid → 1-{2-Amino-6-[(2-aminoethyl)amino]pyridin-3-yl}-2,2,2-trifluoroethanone hydrochloride

HRID 2389796Notes

Reaction equation

HRID 2389796 reaction equation
C(OC([NH:8][CH2:9][CH2:10][NH:11][C:12]1[N:17]=[C:16]([NH:18]C(=O)OC(C)(C)C)[C:15]([C:26](=[O:31])[C:27]([F:30])([F:29])[F:28])=[CH:14][CH:13]=1)=O)(C)(C)C.[ClH:32]>O1CCOCC1>[ClH:32].[NH2:18][C:16]1[C:15]([C:26](=[O:31])[C:27]([F:28])([F:30])[F:29])=[CH:14][CH:13]=[C:12]([NH:11][CH2:10][CH2:9][NH2:8])[N:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57911745tert-Butyl [6-({2-[(tert-butoxycarbonyl)amino]ethyl}amino)-3-(trifluoroacetyl)pyridin-2-yl]carbamate

Product 1

HCID 670603221-{2-Amino-6-[(2-aminoethyl)amino]pyridin-3-yl}-2,2,2-trifluoroethanone hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.5 g (5.57 mmol) of tert-butyl [6-({2-[(tert-butoxycarbonyl)amino]ethyl}amino)-3-(trifluoroacetyl)pyridin-2-yl]carbamate (Example 114A) dissolved in 15 ml of 4N hydrogen chloride in dioxane and stirred for 20 h. The reaction mixture is concentrated to one half, and an equal portion of diethyl ether is added. The reaction mixture is stirred for 20 min, and the product is filtered off and washed with diethyl ether. 1.4 g (89% of theory) of the product are obtained as a solid.

Workup

  1. concentrationThe reaction mixture is concentrated to one half
  2. additionan equal portion of diethyl ether is added
  3. stirringThe reaction mixture is stirred for 20 min
  4. filtrationthe product is filtered off
  5. washwashed with diethyl ether
  6. custom1.4 g (89% of theory) of the product are obtained as a solid

Sources & evidence

ORD record
ord-854b407ebb7c4f4ca969daa039a6ef43
Source dataset
uspto-grants-2012_09
Patent number
US08273752B2

Reaction notes

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