4-Methylmorpholine → HCID 18680124, compound

HRID 564095Notes

Reaction equation

HRID 564095 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18](O)=[O:19])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:21][O:22][NH:23][CH3:24].CN1CCOCC1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>CO>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18](=[O:19])[N:23]([O:22][CH3:21])[CH3:24])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 14232N,O-DimethylhydroxylamineHCID 113578872-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acidHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate

Product 1

HCID 18680124HCID 18680124, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 2.00 g (7.21 mmol) 3,4-dihydro-1H-isoquinoline-2,6-dicarboxylic acid 2-tert-butyl ester in 70 mL MeOH is added at RT 844 mg (8.65 mmol) O,N-dimethyl-hydroxylamine and 1.59 mL (14.4 mmol) 4-methyl-morpholine. The mixture is stirred at RT and then 2.10 g (7.57 mmol) 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methyl-morpholin-4-ium chloride hydrate is added and the mixture is stirred overnight at RT. The residue is directly purified via reverse HPLC chromatography (Waters XBridge, C18; water (0.3% NH4OH)/acetonitrile (0.3% NH4OH) 90:10 to 10:90).

Workup

  1. stirringthe mixture is stirred overnight at RT
  2. customThe residue is directly purified via reverse HPLC chromatography (Waters XBridge, C18; water (0.3% NH4OH)/acetonitrile (0.3% NH4OH) 90:10 to 10:90)

Sources & evidence

ORD record
ord-5dfed17fa6414ec0a2af8c145c82fe6d
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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