Cyclopropanemethanamine → HCID 69145292, compound

HRID 2218254Notes

Reaction equation

HRID 2218254 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([N:21]([CH3:23])[CH3:22])=[C:14]([NH:16][C:17](=[O:20])[CH2:18]Cl)[CH:15]=2)[CH:5]=[C:4]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[N:3]=1.[NH2:40][CH2:41][CH:42]1[CH2:44][CH2:43]1>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([N:21]([CH3:23])[CH3:22])=[C:14]([NH:16][C:17](=[O:20])[CH2:18][NH:40][CH2:41][CH:42]3[CH2:44][CH2:43]3)[CH:15]=2)[CH:5]=[C:4]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[N:3]=1

Participants

4

Reactant 2

HCID 75646CyclopropanemethanamineHCID 69146822HCID 69146822, compound

Product 1

HCID 69145292HCID 69145292, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of N-[5-(2-amino-3-cyano-6-{2-[(4-methoxybenzyl)oxy]phenyl}-4-pyridinyl)-2-(dimethylamino)phenyl]-2-chloroacetamide (0.400 g, 0.738 mmol) in DMF (5 mL) was added aminomethylcyclopropane (0.192 mL, 2.214 mmol). The mixture was stirred at 60° C. for 2 hrs. After cooled to room temperature, the mixture was extracted with ethyl acetate and water. The separated organic phase was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification was carried out by column chromatography on silica gel (chloroform:methanol=100:2, hexane:ethyl acetate=1:2-1:3-1:5, 2 times) to give N1-[5-(2-amino-3-cyano-6-{2-[(4-methoxybenzyl)oxy]phenyl}-4-pyridinyl)-2-(dimethylamino)phenyl]-N2-(cyclopropylmethyl)-glycinamide as a yellow oil (0.130 g, yield 30%).

Workup

  1. temperatureAfter cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate and water
  3. washThe separated organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification

Sources & evidence

ORD record
ord-d68daf7fb4a2495ea914459619c4974b
Source dataset
uspto-grants-2008_08
Patent number
US07410986B2

Reaction notes

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