N-methyl-2-pyrrolidone → HCID 71285550, compound

HRID 536506Notes

Reaction equation

HRID 536506 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:12]=[C:13](I)[C:14]4[C:19]([CH3:21])([CH3:20])[C:18](=[O:22])[NH:17][C:15]=4[N:16]=3)=[N:9][N:8]([CH2:24][C:25]3[C:30]([F:31])=[CH:29][CH:28]=[CH:27][N:26]=3)[C:5]2=[N:6][CH:7]=1.C[N:33]1[CH2:37][CH2:36][CH2:35][C:34]1=O>NCC1CC1>[CH:36]1([CH2:37][NH:33][C:13]2[C:14]3[C:19]([CH3:21])([CH3:20])[C:18](=[O:22])[NH:17][C:15]=3[N:16]=[C:11]([C:10]3[C:4]4[C:5](=[N:6][CH:7]=[C:2]([F:1])[CH:3]=4)[N:8]([CH2:24][C:25]4[C:30]([F:31])=[CH:29][CH:28]=[CH:27][N:26]=4)[N:9]=3)[N:12]=2)[CH2:34][CH2:35]1

Participants

4

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 71503129HCID 71503129, compound

Product 1

HCID 71285550HCID 71285550, compound

Reagents, catalysts & solvents 1

HCID 75646CyclopropanemethanamineSolvent

Conditions

Temperature
150 °C

Procedure

200 mg (0.206 mmol, approx. 55% purity) of the compound obtained in example 21A was dissolved in 1-methyl-2-pyrrolidone (4 ml) in a reaction vessel suitable for a microwave and 1 ml of aminomethylcyclopropane was added. Then it was sealed with a corresponding septum and it was heated in the microwave at 150° C. for 3 h. After cooling, the reaction mixture was purified by preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient). 64 mg of the title compound was obtained (65% of theor.).

Workup

  1. additionwas added
  2. customThen it was sealed with a corresponding septum and it
  3. temperatureAfter cooling
  4. customthe reaction mixture was purified by preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient)

Sources & evidence

ORD record
ord-22405cceecd2467e9155e9de941a7f49
Source dataset
uspto-grants-2014_10
Patent number
US08859569B2

Reaction notes

Loading…