4-Methylmorpholine → HCID 67227628, compound

HRID 2366408Notes

Reaction equation

HRID 2366408 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]([CH2:58][CH3:59])[CH2:55][CH2:56][NH2:57])[CH3:53]>C(Cl)Cl>[ClH:34].[CH2:52]([N:54]([CH2:58][CH3:59])[CH2:55][CH2:56][NH:57][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

Reactant 4

HCID 79724-Methylmorpholine2×HCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 60993N,N-DiethylethylenediamineHCID 86634875HCID 86634875, compound

Product 1

HCID 67227628HCID 67227628, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 18 (235 mg) was dissolved in methylene chloride (10 mL), and 2-chloro-4,6-dimethoxy-1,3,5-triazine (105 mg) and N-methylmorpholine (66 μL) were added to the solution, followed by stirring for 30 minutes with ice cooling. Subsequently, N,N-diethylethylenediamine (85 μL) and N-methylmorpholine (110 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: 287 mg, 95%).

Workup

  1. stirringby stirring at room temperature for 17 hours
  2. customThe solvent was evaporated to dryness
  3. customthe residue was purified by silica gel column chromatography (CHCl3-MeOH)

Sources & evidence

ORD record
ord-653c6f1f165c487b936a20dd96f5fe72
Source dataset
uspto-grants-2014_04
Patent number
US08697742B2

Reaction notes

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