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

HRID 2088661Notes

Reaction equation

HRID 2088661 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[C:13]([C:14](=[O:17])[CH2:15][CH3:16])=[CH:12][CH:11]=[C:10](Cl)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:20]([NH:27][CH2:28][CH2:29][NH2:30])([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].C(N(CC)C(C)C)(C)C>CS(C)=O.C(OCC)(=O)C.O>[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[C:13]([C:14](=[O:17])[CH2:15][CH3:16])=[CH:12][CH:11]=[C:10]([NH:30][CH2:29][CH2:28][NH:27][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamineHCID 57911766tert-Butyl (6-chloro-3-propanoylpyridin-2-yl)carbamate

Product 1

HCID 57911744tert-Butyl[6-({2-[(tert-butoxycarbonyl)amino]ethyl}amino)-3-propanoylpyridin-2-yl]carbamate

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

730 mg (2.4 mmol) of tert-butyl(6-chloro-3-propanoylpyridin-2-yl)carbamate (Example 23A) were initially charged in 7 ml of DMSO, and 512 mg (3.2 mmol) of N-Boc-ethylenediamine and 640 μl (3.7 mmol) of N,N-diisopropylethylamine were added. The reaction mixture was irradiated in the microwave reactor at 90° C. for 45 min. The reaction mixture was taken up in a mixture of ethyl acetate and water. The organic phase was washed with saturated aqueous ammonium chloride solution and then with saturated aqueous sodium bicarbonate 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 530 mg (53% of theory) of the product as a solid.

Workup

  1. customThe reaction mixture was irradiated in the microwave reactor at 90° C. for 45 min
  2. washThe organic phase was washed with saturated aqueous ammonium chloride solution
  3. dry with materialwith saturated aqueous sodium bicarbonate solution, dried 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-108d0b116d324d52b67783b3813635e6
Source dataset
uspto-grants-2013_05
Patent number
US08436003B2

Reaction notes

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