Morpholine → HCID 58626123, compound

HRID 1161688Notes

Reaction equation

HRID 1161688 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)[N:5]=[C:4]([C:20]2[CH:21]=[C:22]([C:26](=[O:28])[CH3:27])[CH:23]=[CH:24][CH:25]=2)[N:3]=1.[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>C(O)CCC>[N:29]1([C:2]2[CH:7]=[C:6]([NH:8][C:9]3[CH:10]=[CH:11][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:13][CH:14]=3)[N:5]=[C:4]([C:20]3[CH:21]=[C:22]([C:26](=[O:28])[CH3:27])[CH:23]=[CH:24][CH:25]=3)[N:3]=2)[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 58626079HCID 58626079, compound

Product 1

HCID 58626123HCID 58626123, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of compound 1-{3-[4-chloro-6-(4-trifluoromethoxy-phenylamino)-pyrimidin-2-yl]-phenyl}-ethanone (0.13 g, 0.32 mmol) and morpholine (0.22 g, 2.55 mmol) in n-butanol (10 mL) was refluxed for 24 hours under nitrogen atmosphere. The mixture was cooled to temperature in the range of 20-40° C. and concentrated under vacuum. The crude compound was purified by column chromatography using 18-20% ethylacetate in petroleum ether to afford the desired compound (0.11 g, 75%) as a white solid.

Workup

  1. temperaturewas refluxed for 24 hours under nitrogen atmosphere
  2. concentrationconcentrated under vacuum
  3. customThe crude compound was purified by column chromatography

Sources & evidence

ORD record
ord-08eaf4319905463a91c767c120e724a2
Source dataset
uspto-grants-2010_10
Patent number
US07820654B2

Reaction notes

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