HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Propargyl alcohol → 1H,7H-Pyrido[1,2,3-de]quinoxaline-6-carboxamide, N-[(4-chlorophenyl)methyl]-2,3-dihydro-9-(3-hydroxy-1-propynyl)-1-methyl-2,7-dioxo-

HRID 1168519
Notes
Print preview

Reaction equation

HRID 1168519 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].[Cl:5][C:6]1[CH:32]=[CH:31][C:9]([CH2:10][NH:11][C:12]([C:14]2[C:15](=[O:30])[C:16]3[C:17]4[N:18]([CH:29]=2)[CH2:19][C:20](=[O:28])[N:21]([CH3:27])[C:22]=4[CH:23]=[C:24](I)[CH:25]=3)=[O:13])=[CH:8][CH:7]=1>C(NCC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:5][C:6]1[CH:32]=[CH:31][C:9]([CH2:10][NH:11][C:12]([C:14]2[C:15](=[O:30])[C:16]3[C:17]4[N:18]([CH:29]=2)[CH2:19][C:20](=[O:28])[N:21]([CH3:27])[C:22]=4[CH:23]=[C:24]([C:3]#[C:2][CH2:1][OH:4])[CH:25]=3)=[O:13])=[CH:8][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 7859Propargyl alcoholHCID 12083044N-(4-Chlorobenzyl)-9-iodo-1-methyl-2,7-dioxo-2,3-dihydro-1H,7H-pyrido[1,2,3-de]-quinoxaline-6-carboxamide

Product 1

HCID 101138641H,7H-Pyrido[1,2,3-de]quinoxaline-6-carboxamide, N-[(4-chlorophenyl)methyl]-2,3-dihydro-9-(3-hydroxy-1-propynyl)-1-methyl-2,7-dioxo-

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalyst
HCID 8021
Diethylamine
Solvent

Procedure

Propargyl alcohol (50 mg), cuprous iodide (50 mg) and a solution of PdCl2(PPh3)2 (1 mL, 0.15 M in THF) are added to a suspension of N-(4-chlorobenzyl)-9-iodo-1-methyl-2,7-dioxo-2,3-dihydro-1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxamide (Preparation 23, 250 mg) in diethylamine (2.0 mL). The reaction is stirred for 90 min and the product is then extracted into chloroform and is chromatographed on silica gel. The desired product is eluted with 20% methanol/chloroform. Physical characteristics: 1H NMR (DMSO-d6) δ3.40, 4.36, 4.56, 5.22, 5.42, 7.36, 7.40, 7.44, 7.88, 8.76, 10.2. HRMS m/z 436.1064 (C23H18ClN3O4).

Workup

  1. extractionthe product is then extracted into chloroform
  2. customis chromatographed on silica gel
  3. washThe desired product is eluted with 20% methanol/chloroform

Sources & evidence

ORD record
ord-ec798d0535ed427381cf794d6c54af8a
Source dataset
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06624159B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes