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

HRID 2088649Notes

Reaction equation

HRID 2088649 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[C:13]([C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])=[CH:12][CH:11]=[C:10](Cl)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[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:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[C:13]([C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])=[CH:12][CH:11]=[C:10]([NH:32][CH2:31][CH2:30][NH:29][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

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-chlor-3-(trifluoroacetyl)pyridin-2-yl]carbamate (Example 11A) 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 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 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-05941046c6924279babfb0b0f14052f1
Source dataset
uspto-grants-2013_05
Patent number
US08436003B2

Reaction notes

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