4-Chlorobenzylamine → HCID 178522855, compound

HRID 1168497Notes

Reaction equation

HRID 1168497 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]3[C:21](=[O:22])[C:20]([C:23]([O:25]CC)=O)=[CH:19][N:12]4[CH2:13][C:14](=O)[NH:15][C:16]([CH:17]=2)=[C:11]34)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH2:34])=[CH:31][CH:30]=1>CO>[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH:34][C:23]([C:20]2[C:21](=[O:22])[C:10]3[C:11]4[N:12]([CH:19]=2)[CH2:13][C:14]([NH:34][CH2:33][C:32]2[CH:35]=[CH:36][C:29]([Cl:28])=[CH:30][CH:31]=2)=[N:15][C:16]=4[CH:17]=[C:8]([CH2:7][N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)[CH:9]=3)=[O:25])=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 660364-ChlorobenzylamineHCID 12083024HCID 12083024, compound

Product 1

HCID 178522855HCID 178522855, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of ethyl 9-(4-morpholinylmethyl)-2,7-dioxo-2,3-dihydro-1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxylate (Preparation 4, 280 mg) and 4-chlorobenzylamine (1 mL) is heated at 180° C. The solution is cooled, diluted with methanol (2 mL), and the precipitate is filtered off. The resulting solid is washed with methanol followed by ether and dried to give 117 mg of the title compound. Physical characteristics: 1H NMR (DMSO-d6) δ2.35, 3.49, 3.57, 4.56, 4.60, 5.08, 7.20, 7.34-7.40, 7.64, 8.21, 8.62, 10.6. Anal. Found: C, 62.90; H, 4.99; N, 11.81; Cl, 12.03.

Workup

  1. temperatureThe solution is cooled
  2. filtrationthe precipitate is filtered off
  3. washThe resulting solid is washed with methanol
  4. customdried

Sources & evidence

ORD record
ord-32c38d08b002411a8039ae4b8fb9f3f0
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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