4-Methylmorpholine → HCID 67226848, compound
Reaction equation
[C:1](/[C:3](/[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=1)=[CH:4]\[C:5]1[S:9][C:8]([N:10]2[CH2:15][CH2:14][CH:13]([O:16][C:17](=[O:23])[CH2:18][CH2:19][C:20]([O-:22])=O)[CH2:12][CH2:11]2)=[CH:7][CH:6]=1)#[N:2].[Cl:34]C1N=C(OC)N=C(OC)N=1.CN1CCOCC1.[CH2:52]([N:54]([CH2:59][CH3:60])[CH2:55][CH2:56][NH:57][CH3:58])[CH3:53]>C(Cl)Cl>[ClH:34].[CH2:52]([N:54]([CH2:59][CH3:60])[CH2:55][CH2:56][N:57]([CH3:58])[C:20](=[O:22])[CH2:19][CH2:18][C:17]([O:16][CH:13]1[CH2:12][CH2:11][N:10]([C:8]2[S:9][C:5](/[CH:4]=[C:3](\[C:1]#[N:2])/[C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=3)=[CH:6][CH:7]=2)[CH2:15][CH2:14]1)=[O:23])[CH3:53]Participants
6
Procedure
Compound 18 (500 mg) was dissolved in methylene chloride (10 mL), and 2-chloro-4,6-dimethoxy-1,3,5-triazine (224 mg) and N-methylmorpholine (129 μL) were added to the solution, followed by stirring with ice cooling for 30 minutes. Subsequently, N,N-diethyl-N′-methylethylenediamine (166 μL) and N-methylmorpholine (215 μL) were added to the mixture, followed by stirring at room temperature for 17 hours. The solvent was evaporated to dryness, and the residue was purified by silica gel column chromatography (CHCl3-MeOH), to thereby yield the target product (yield: 503 mg, 76%).
Workup
- stirringby stirring at room temperature for 17 hours
- customThe solvent was evaporated to dryness
- customthe residue was purified by silica gel column chromatography (CHCl3-MeOH)
Sources & evidence
- ORD record
- ord-85dc6f89925f47a9b0468d0ff5ab5408
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697742B2
Reaction notes
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