Morpholine → HCID 83074581, compound

HRID 1479828

Reaction equation

HRID 1479828 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([Cl:10])[N:3]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.FC1C=CC(S(N(CC)C(=C)C(NCC2C=CN=C(C3C=CC(OC(F)(F)F)=CC=3)C=2)=O)(=O)=O)=CC=1>C(O)C.ClC1SC(S(N(CC)C(=C)C(NCC2C=CN=C(C3C=CC(OC(F)(F)F)=CC=3)C=2)=O)(=O)=O)=CC=1>[Cl:10][C:4]1[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=[C:2]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[N:3]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 7359062,6-DichloroisonicotinonitrileHCID 783199092-[(4-fluorophenyl)sulfonyl-ethyl-amino]-N-[[2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methyl]prop-2-enamide

Product 1

HCID 83074581HCID 83074581, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 78319913HCID 78319913, compoundSolvent

Conditions

Temperature
70 °C

Procedure

2,6-dichloropyridine-4-carbonitrile 24 (4 gr, 23.13 mmol) was dissolved in 100 ml of ethanol. To the solution were added TEA (1 equiv., 3.22 ml), morpholine (1 equiv., 2 ml) and the mixture was stirred at 70° C. for 4 hours. (TLC AcOEt 3/petroleum ether 7). The solvent was evaporated and the residue was dissolved with ethyl acetate, washed with water and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The crude was crystallized from ethyl acetate and petroleum ether to give a beige solid. (4.6 g, 89% yield) 1HNMR (DMSO, 400 MHz) δ 3.58 (4H, m), 3.64 (4H, m), 7.10 (1H, s), 7.32 (1H, s)

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe crude was crystallized from ethyl acetate and petroleum ether
  7. customto give a beige solid

Sources & evidence

ORD record
ord-aa930a730be148839c0def30ec789bd8
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Linked notes

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