Dimethyl Sulfoxide → tert-Butyl [6-({2-[(tert-butoxycarbonyl)amino]ethyl}amino)-3-(trifluoroacetyl)pyridin-2-yl]carbamate

HRID 2389795Notes

Reaction equation

HRID 2389795 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:5]([C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])=[CH:4][CH:3]=1.CS(C)=O.[C:26]([NH:33][CH2:34][CH2:35][NH2:36])([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].C(N(CC)C(C)C)(C)C>C(OCC)(=O)C.O>[C:29]([O:28][C:26]([NH:33][CH2:34][CH2:35][NH:36][C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:5]([C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])=[CH:4][CH:3]=1)=[O:27])([CH3:32])([CH3:31])[CH3:30]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamineHCID 57911758tert-Butyl[6-chloro-3-(trifluoroacetyl)pyridin-2-yl]carbamate

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

5 g (15.4 mmol) of tert-butyl [6-chloro-3-(trifluoroacetyl)pyridin-2-yl]carbamate (Example 113A) are introduced into 37.5 ml of DMSO, and 3.2 g (20 mmol) of N-Boc-ethylenediamine and 4 ml (23 mmol) of N,N-diisopropylethylamine are added. The reaction mixture is irradiated in a microwave reactor at 90° C. for 0.5 h. The reaction mixture is taken up in a mixture of ethyl acetate and water. The organic phase is washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated in a rotary evaporator. The reaction mixture is chromatographed on silica gel (mobile phase cyclohexane/ethyl acetate 5:1→1:1). 2.5 g (34% of theory) of the product are obtained as a solid.

Workup

  1. additionare added
  2. customThe reaction mixture is irradiated in a microwave reactor at 90° C. for 0.5 h
  3. washThe organic phase is washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated in a rotary evaporator
  6. customThe reaction mixture is chromatographed on silica gel (mobile phase cyclohexane/ethyl acetate 5:1→1:1)
  7. custom2.5 g (34% of theory) of the product are obtained as a solid

Sources & evidence

ORD record
ord-6e82ff5b003b4b548b7d2d8bc6cf01db
Source dataset
uspto-grants-2012_09
Patent number
US08273752B2

Reaction notes

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