4-Methylmorpholine → HCID 89698233, compound

HRID 1054195Notes

Reaction equation

HRID 1054195 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:10]=[CH:9][O:8][C:7]=1[C:11]([OH:13])=O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.CN1CCOCC1.Cl.[CH3:40][NH:41][C:42]([C@@H:44]1[NH:56][CH2:55][C:47]2[NH:48][C:49]3[C:54]([C:46]=2[CH2:45]1)=[CH:53][CH:52]=[CH:51][CH:50]=3)=[O:43]>CC#N.C(OCC)(=O)C>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[CH:10]=[CH:9][O:8][C:7]=1[C:11]([N:56]1[C@@H:44]([C:42]([NH:41][CH3:40])=[O:43])[CH2:45][C:46]2[C:54]3[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=3)[NH:48][C:47]=2[CH2:55]1)=[O:13]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 89691271HCID 89691271, compoundHCID 117773657HCID 117773657, compound

Product 1

HCID 89698233HCID 89698233, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of product (3-A) (2.19 g, 11.9 mmol) in CH3CN (200 ml) was added 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium chloride (DMTMMCl, 4.9 g, 17.8 mmol), and then 4-methylmorpholine (NMM, 4.8 g, 47.6 mmol) was added drop-wise while maintaining the temperature below 20° C. After stirring for 16 h at rt, product (5-A) (3 g, 13.1 mmol) was added, and the solution was stirred at rt for another 6 h. The reaction mixture was diluted with ethyl acetate (200 mL), washed with brine (100 mL), dried over Na2SO4, and concentrated and purified by CC (DCM:MeOH=200:1 to 100:1) to give product (6-A) (2.2 g, 47%) as a brown solid. LC-MS (M+H)+=396.

Workup

  1. temperaturewhile maintaining the temperature below 20° C
  2. stirringthe solution was stirred at rt for another 6 h
  3. washwashed with brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by CC (DCM:MeOH=200:1 to 100:1)

Sources & evidence

ORD record
ord-c10c3e3360954207aa7b2d8151bbfbcb
Source dataset
uspto-grants-2016_07
Patent number
US09394296B2

Reaction notes

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