Diisopropylethylamine → HCID 68508908, compound

HRID 1715119Notes

Reaction equation

HRID 1715119 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([O:23][CH2:24][CH:25]=[CH2:26])=[O:22])=[CH:17][C:16]=2[NH:27][C:28](=[O:31])[CH2:29]Br)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)C(C)C)C>C1(C)C=CC=CC=1>[CH2:24]([O:23][C:21]([C:18]1[CH:17]=[C:16]2[C:15](=[CH:20][CH:19]=1)[N:14]([CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]1)[CH2:29][C:28](=[O:31])[NH:27]2)=[O:22])[CH:25]=[CH2:26]

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 68511063HCID 68511063, compound

Product 1

HCID 68508908HCID 68508908, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-[4-allyloxycarbonyl-2-(2-bromo-acetylamino)-phenylamino]-piperidine-1-carboxylic acid tert-butyl ester (23.0 g, 46.33 mmol, 1.0 equiv) and N-ethyldiisopropylamine (11.98 g, 92.67 mmol,2.0 equiv) in toluene (250 mL) was heated to reflux. After 8 h, the reaction mixture was cooled, washed with water and concentrated by evaporation under reduced pressure and purified with silica column chromatography eluting with dichloromethane/acetone (95:5) to obtain 10.0 g (52%) of the title compound as yellow solid. 1H NMR (400 MHz, DMSO): δ 1.41 (s, 9H), 1.65 (br s, 4H), 2.89 (s, 2H), 3.74 (s, 2H), 3.90 (br s, 1H), 4.05 (br s, 2H), 4.73 (d, J=5.1, 2H), 5.25 (d, J=10.4, 1H), 5.36 (dd, J=17.2 Hz, J=1.1 Hz, 1H), 5.98-6.05 (m, 1H), 6.95 (d, J=8.7 Hz, 1H), 7.44 (d, J=1.4 Hz, 1H), 7.53 (dd, J=17.2 Hz, J=1.1 Hz, 1H), 10.58 (s, 1H). 13C-NMR (100 MHz, DMSO): δ 26.87, 28.02, 45.15, 53.36, 64.35, 78.67, 110.81, 115.77, 117.36, 118.04, 125.21, 126.61, 132.95, 132.99, 138.63, 153.70, 164.94, 165.00. MS (ISP): 416.2 [M+H]+.

Workup

  1. temperaturewas heated to reflux
  2. temperaturethe reaction mixture was cooled
  3. washwashed with water
  4. concentrationconcentrated by evaporation under reduced pressure
  5. custompurified with silica column chromatography
  6. washeluting with dichloromethane/acetone (95:5)

Sources & evidence

ORD record
ord-fe37b5170ab04483b691afb3af62b847
Source dataset
uspto-grants-2010_09
Patent number
US07799806B2

Reaction notes

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