Benzylamine → HCID 18790701, compound

HRID 1075515Notes

Reaction equation

HRID 1075515 reaction equation
[O:1]=[C:2]1[NH:7][C:6]2[C:8]3[CH:9]=[CH:10][C:11]([CH2:15][C:16]([O:18]CC)=O)=[CH:12][C:13]=3[CH2:14][C:5]=2[N:4]2[CH:21]=[CH:22][N:23]=[C:3]12.[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl>[CH2:24]([NH:31][C:16](=[O:18])[CH2:15][C:11]1[CH:10]=[CH:9][C:8]2[C:6]3[NH:7][C:2](=[O:1])[C:3]4[N:4]([CH:21]=[CH:22][N:23]=4)[C:5]=3[CH2:14][C:13]=2[CH:12]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 54131470HCID 54131470, compound

Product 1

HCID 18790701HCID 18790701, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 0.618 g of ethyl [4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-8-yl]acetate and 10 ml of benzylamine is heated at 140° C. for 17 hours under a nitrogen atmosphere. After returning to room temperature, 50 ml of dichloromethane are added to the reaction mixture. The solid formed is filtered, washed with dichloromethane and then recrystallized from 25 ml of dimethylformamide. After drying under reduced pressure (1 mbar) at 60° C., 0.65 g of N-benzyl-2-(4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-8-yl)acetamide is thus obtained, which product has a melting point greater than 260° C. (Analysis; % Calculated C: 71.34, H: 4.90, N: 15.13, O: 8.64; % Calculated C: 71.1, H: 5.0, N: 15.2, O: 9.1).

Workup

  1. customAfter returning to room temperature
  2. customThe solid formed
  3. filtrationis filtered
  4. washwashed with dichloromethane
  5. customrecrystallized from 25 ml of dimethylformamide
  6. customAfter drying under reduced pressure (1 mbar) at 60° C.

Sources & evidence

ORD record
ord-bb87cfee55dd4a719f6946f957dd7c68
Source dataset
uspto-grants-1999_05
Patent number
US05902803

Reaction notes

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