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

HRID 444834Notes

Reaction equation

HRID 444834 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.[C:22]([NH:29][CH2:30][CH2:31][NH2:32])([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C(N(CC)C(C)C)(C)C>CS(C)=O.C(OCC)(=O)C.O>[C:25]([O:24][C:22]([NH:29][CH2:30][CH2:31][NH:32][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:23])([CH3:28])([CH3:27])[CH3:26]

Participants

7

Reactant 3

HCID 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 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

5 g (15.4 mmol) of tert-butyl [6-chloro-3-(trifluoroacetyl)pyridin-2-yl]carbamate (Example 32A) were initially charged in 37.5 ml of DMSO, and 3.2 g (20 mmol) of N-Boc-ethylenediamine and 4 ml (23 mmol) of N,N-diisopropylethylamine were added. The reaction mixture was irradiated in a microwave reactor at 90° C. for 0.5 h. The reaction mixture was taken up in a mixture of ethyl acetate and water. The organic phase was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated on a rotary evaporator. The reaction mixture was chromatographed on silica gel (mobile phase cyclohexane/ethyl acetate 5:1→1:1). This gave 2.5 g (34% of theory) of the product as a solid.

Workup

  1. customThe reaction mixture was irradiated in a microwave reactor at 90° C. for 0.5 h
  2. washThe organic phase was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated on a rotary evaporator
  5. customThe reaction mixture was chromatographed on silica gel (mobile phase cyclohexane/ethyl acetate 5:1→1:1)

Sources & evidence

ORD record
ord-483b19ad22784d83af95d6ed3f958079
Source dataset
uspto-grants-2013_07
Patent number
US08476267B2

Reaction notes

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