(3-{6-Amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl)-prop-2-ynyl)-carbamic acid tert-butyl ester → 5-(3-Amino-prop-1-ynyl)-3-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-2-ylamine

HRID 2266670Notes

Reaction equation

HRID 2266670 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]#[C:10][C:11]1[CH:12]=[N:13][C:14]([NH2:29])=[C:15]([O:17][CH:18]([C:20]2[C:25]([Cl:26])=[CH:24][CH:23]=[C:22]([F:27])[C:21]=2[Cl:28])[CH3:19])[CH:16]=1)(C)(C)C>C(O)(C(F)(F)F)=O.ClCCl>[NH2:7][CH2:8][C:9]#[C:10][C:11]1[CH:16]=[C:15]([O:17][CH:18]([C:20]2[C:25]([Cl:26])=[CH:24][CH:23]=[C:22]([F:27])[C:21]=2[Cl:28])[CH3:19])[C:14]([NH2:29])=[N:13][CH:12]=1

Participants

4

Reactant 1

HCID 58885785(3-{6-Amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl)-prop-2-ynyl)-carbamic acid tert-butyl ester

Product 1

HCID 211114705-(3-Amino-prop-1-ynyl)-3-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-2-ylamineYield 93%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The solution of (3-{6-Amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-prop-2-ynyl)-carbamic acid tert-butyl ester in 25% TFA in dichloromethane was stirred for 2 hr, then washed by 2N NaOH, water twice, brine, dried over Na2SO4. After filtration and evaporation, 5-(3-amino-prop-1-ynyl)-3-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-2-ylamine was obtained in 93% yield.

Workup

  1. washwashed by 2N NaOH, water twice
  2. dry with materialbrine, dried over Na2SO4
  3. filtrationAfter filtration and evaporation

Sources & evidence

ORD record
ord-c8eecdac5c034ac7ac5ecd31c53cf84c
Source dataset
uspto-grants-2010_12
Patent number
US07858643B2

Reaction notes

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