Morpholine → HCID 89601598, compound

HRID 514217Notes

Reaction equation

HRID 514217 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][CH3:10])[CH:5]=[C:4]([Cl:11])[C:3]=1[C:12]1[C:13](=[O:26])[CH:14]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:15][C:16]=1[O:17]C.N1CCOCC1>>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][CH3:10])[CH:5]=[C:4]([Cl:11])[C:3]=1[CH:12]1[C:13](=[O:26])[CH:14]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:15][C:16]1=[O:17]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 89600926HCID 89600926, compound

Product 1

HCID 89601598HCID 89601598, compoundYield 36%

Conditions

Temperature
10 °C

Procedure

A mixture of 2-(2,6-dichloro-4-prop-1-ynyl-phenyl)-3-methoxy-5-(2-pyridylmethyl)cyclopent-2-en-1-one (41 mg, 0.106 mmol) and morpholine (1 ml) were heated at 10°C. for 4 hours. The reaction was cooled to room temperature and evaporated to dryness under reduced pressure. The residue was partitioned between EtOAc (10 ml) and saturated aqueous NH4Cl (10 ml). The organic phase was washed with further saturated aqueous NH4Cl (5 ml), brine (5 ml), dried over MgSO4, filtered and evaporated to dryness under reduced pressure. The crude product was purified on the FractionLynx to give the desired product (14 mg, 36%). 1H NMR (400 MHz, CDCl3) δ ppm 8.50 (d, 1H), 7.85 (dd, 1H), 7.40 (d, 1H), 7.35-7.30 (m, 3H), 6.10 (br, 1H), 3.40-3.25 (m, 3H), 3.05 (dd, 1H), 2.40 (dd, 1H), 2.05 (s, 3H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customevaporated to dryness under reduced pressure
  3. customThe residue was partitioned between EtOAc (10 ml) and saturated aqueous NH4Cl (10 ml)
  4. washThe organic phase was washed with further saturated aqueous NH4Cl (5 ml), brine (5 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness under reduced pressure
  8. customThe crude product was purified on the FractionLynx

Sources & evidence

ORD record
ord-2c2cf6680f8b400ca4c3437ba3c7f762
Source dataset
uspto-grants-2015_08
Patent number
US09107415B2

Reaction notes

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