Diisopropylethylamine → HCID 86666752, compound

HRID 1804617Notes

Reaction equation

HRID 1804617 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:12][CH2:13]Cl)[C:5](=[O:11])[O:6][C:7]([CH3:10])(C)C.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1([NH2:24])[CH2:23][CH2:22]1.[CH:25](N(CC)C(C)C)(C)[CH3:26]>CN(C)C=O>[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1([N:24]2[CH2:2][CH2:3][N:4]([C:5]([O:6][CH2:7][CH2:10][CH2:25][CH3:26])=[O:11])[CH2:12][CH2:13]2)[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 111054091-(Pyridin-2-yl)cyclopropanamineHCID 11230235N-BOC-N,N-Bis(2-chloroethyl)amine

Product 1

HCID 86666752HCID 86666752, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred suspension of 0.32 g (1.3 mmol) of tert-butyl bis(2-chloroethyl)carbamate in 5 ml of N,N-diisopropylethylamine and 0.5 mL of anhydrous N,N-dimethylformamide was added 0.23 g (1.1 mmol) of 1-pyridin-2-ylcyclopropanamine, bis(hydrochloride) salt and the resulting mixture was heated to 100° C. for 15 h. The mixture was cooled to ambient temperature, quenched with water, and the aqueous phase extracted with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness. The residue was purified by silica gel chromatography eluting with 50% acetone/hexanes mixture to afford the title compound as yellow gum (0.055 g, 17% yield). 1H-NMR (500 MHz, CDCl3) δ 8.55 (d, J=4.7 Hz, 1H), 7.61 (td, J=7.7, 1.7 Hz, 1H), 7.33 (d, J=7.9, 4.6 Hz, 1H), 7.12 (dd, J=7.4, 4.9 Hz, 1H), 3.37-3.35 (m, 4H), 2.60-2.58 (m, 4H), 1.41 (s, 9H), 1.05-1.03 (m, 4H). LC-MS: m/z (ES) 304.5 (MH)+.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customquenched with water
  3. extractionthe aqueous phase extracted with ethyl acetate
  4. washThe combined organics were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with 50% acetone/hexanes mixture

Sources & evidence

ORD record
ord-c346ee2b424e432aa8b3bcb3606fc673
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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