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

HRID 444835Notes

Reaction equation

HRID 444835 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 33A) were dissolved in 15 ml of a 4N solution of hydrogen chloride in dioxane, and the mixture was stirred for 20 h. The reaction mixture was concentrated to half of its original volume and the same amount of diethyl ether was added. The reaction mixture was stirred for 20 min and the product was filtered off and washed with diethyl ether. This gave 1.4 g (89% of theory) of the product as a solid.

Workup

  1. concentrationThe reaction mixture was concentrated to half of its original volume
  2. additionthe same amount of diethyl ether was added
  3. stirringThe reaction mixture was stirred for 20 min
  4. filtrationthe product was filtered off
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-78f5183a69f54730bd9ba8062ca9a761
Source dataset
uspto-grants-2013_07
Patent number
US08476267B2

Reaction notes

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