Acetonitrile → HCID 118162408, compound

HRID 707528Notes

Reaction equation

HRID 707528 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[N:11]=[C:10]([N:12]2[CH2:15][CH:14]([N:16]([CH3:25])[CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[CH2:13]2)[CH:9]=[CH:8][CH:7]=1.C(#N)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH3:25][N:16]([CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)[CH:14]1[CH2:13][N:12]([C:10]2[N:11]=[C:6]([CH:2]=[O:1])[CH:7]=[CH:8][CH:9]=2)[CH2:15]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 521998p-Toluenesulfonic acid monohydrateHCID 118162471HCID 118162471, compound

Product 1

HCID 118162408HCID 118162408, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixed solution of 1-(6-(1,3-dioxolan-2-yl)pyridin-2-yl)-N-methyl-N-(2-(morpholin-4-yl)ethyl)azetidine-3-amine (157 mg, 0.451 mmol) described in Production Example 29-3, acetonitrile (5.00 mL) and water (0.500 mL) was added p-toluenesulfonic acid monohydrate (386 mg, 2.03 mmol). The resultant mixture was stirred at 100° C. for 5 hours. The mixture was cooled to room temperature, and then the solvent was evaporated under a reduced pressure. A saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the resultant solution was extracted with dichloromethane three times. An organic layer was dried over anhydrous magnesium sulfate and then filtrated. The solvent was evaporated under a reduced pressure to give a crude product (122 mg) of the title compound. The product was used in the subsequent reaction without further purification.

Workup

  1. customthe solvent was evaporated under a reduced pressure
  2. additionA saturated aqueous sodium hydrogen carbonate solution was added to the residue
  3. extractionthe resultant solution was extracted with dichloromethane three times
  4. dry with materialAn organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltrated
  6. customThe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-d319293fb3c540048db1fc517a3120f4
Source dataset
uspto-grants-2015_11
Patent number
US09174998B2

Reaction notes

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