4-Methylmorpholine → HCID 178430522, compound

HRID 1678075Notes

Reaction equation

HRID 1678075 reaction equation
[CH3:1]/[C:2](=[CH:11]\[N:12]1[CH2:17][CH2:16][CH2:15]CC1)/[C:3]([NH:5][C:6](=[O:10])OCC)=[S:4].Cl.[C:19]([C:23]1[N:28]=[C:27]([N:29]2[CH2:34][CH2:33][N:32](CCCN)[CH2:31][CH2:30]2)[CH:26]=[C:25]([C:39]([F:42])([F:41])[F:40])[N:24]=1)([CH3:22])([CH3:21])[CH3:20].CN1CCOCC1>CO>[C:19]([C:23]1[N:28]=[C:27]([N:29]2[CH2:30][CH2:31][N:32]([CH2:15][CH2:16][CH2:17][N:12]3[CH:11]=[C:2]([CH3:1])[C:3]([SH:4])=[N:5][C:6]3=[O:10])[CH2:33][CH2:34]2)[CH:26]=[C:25]([C:39]([F:40])([F:41])[F:42])[N:24]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 67372784HCID 67372784, compoundHCID 86608507HCID 86608507, compound

Product 1

HCID 178430522HCID 178430522, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.7 g (2.7 mmol) of ethyl (2E)-2-methyl-3-piperidin-1-ylprop-2-enethioylcarbamate (WO 00/61579), 0.9 g (2.6 mmol) of 3-{4-[2-tert-butyl-6-(trifluoromethyl)pyrimidin-4-yl]piperazin-1-yl}propan-1-amine hydrochloride from Example 1.2 and 0.6 g (5.5 mmol) of N-methylmorpholine in 20 ml of methanol were stirred at room temperature under a nitrogen atmosphere for 12 hours. Insolubles were removed by filtration, washed three times with methanol and water and then recrystallized from ethyl acetate. Drying in vacuo at 50° C. resulted in 0.5 g of the title compound.

Workup

  1. customInsolubles were removed by filtration
  2. washwashed three times with methanol and water
  3. customrecrystallized from ethyl acetate
  4. customDrying in vacuo at 50° C.

Sources & evidence

ORD record
ord-061d1ae0dc884dba8a9882949dc43803
Source dataset
uspto-grants-2011_08
Patent number
US08008488B2

Reaction notes

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