Hydrochloric Acid → 1-[2-Amino-6-(piperidin-3-ylamino)pyridin-3-yl]-2,2,2-trifluoroethanone hydrochloride

HRID 1182998Notes

Reaction equation

HRID 1182998 reaction equation
C(OC([NH:8][C:9]1[N:14]=[C:13]([NH:15][CH:16]2[CH2:21][CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]2)[CH:12]=[CH:11][C:10]=1[C:29](=[O:34])[C:30]([F:33])([F:32])[F:31])=O)(C)(C)C.[ClH:35]>O1CCOCC1.C(OCC)C>[ClH:35].[NH2:8][C:9]1[C:10]([C:29](=[O:34])[C:30]([F:32])([F:33])[F:31])=[CH:11][CH:12]=[C:13]([NH:15][CH:16]2[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]2)[N:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57911775tert-Butyl 3-({6-[(tert-butoxycarbonyl)amino]-5-(trifluoroacetyl)pyridin-2-yl}amino)piperidine-1-carboxylate

Product 1

HCID 670602981-[2-Amino-6-(piperidin-3-ylamino)pyridin-3-yl]-2,2,2-trifluoroethanone hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

670 mg (1.37 mmol) of tert-butyl 3-({6-[(tert-butoxycarbonyl)amino]-5-(trifluoroacetyl)pyridin-2-yl}amino)piperidine-1-carboxylate (Example 12A) were dissolved in 25 ml of a hydrochloric acid solution in dioxane (4 M) and stirred at RT for 20 h. On completion of reaction, the reaction mixture was diluted with diethyl ether (100 ml), and the precipitate was filtered off completely and washed with diethyl ether (100 ml) and dried. 286 mg (64% of theory) of the product were obtained in solid form.

Workup

  1. customOn completion of reaction
  2. filtrationthe precipitate was filtered off completely
  3. washwashed with diethyl ether (100 ml)
  4. customdried
  5. custom286 mg (64% of theory) of the product were obtained in solid form

Sources & evidence

ORD record
ord-34f9e90f77bc44c095f9b4214b5e43fc
Source dataset
uspto-grants-2014_03
Patent number
US08664246B2

Reaction notes

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