Morpholine → HCID 59362925, compound

HRID 1668818Notes

Reaction equation

HRID 1668818 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[C:21]4[CH2:22][CH2:23][CH2:24][C:20]=4[N:19]=[C:18](Cl)[N:17]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7][CH2:6]1)=[O:4].[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.C(N(C(C)C)CC)(C)C>C(O)(C)C>[CH3:1][O:2][C:3]([C:5]1([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[C:21]4[CH2:22][CH2:23][CH2:24][C:20]=4[N:19]=[C:18]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[N:17]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 59362943HCID 59362943, compound

Product 1

HCID 59362925HCID 59362925, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 1-[4-(2-chloro-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid methyl ester (2 g, 5.594 mmol), morpholine (0.64 mL, 7.27 mmol) and diisopropylethylamine (1.46 mL, 8.392 mmol) in isopropanol (25 mL) was heated at reflux for 50 hours. After cooling to a temperature in the range of 15° C. to 40° C., the precipitated solid was filtered, washed with hexane and dried. The solid was dissolved in ethyl acetate, washed with water, brine, dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure to afford the title compound as a light yellow solid (1.9 g, 83% yield).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 50 hours
  3. temperatureAfter cooling to a temperature in the range of 15° C. to 40° C.
  4. filtrationthe precipitated solid was filtered
  5. washwashed with hexane
  6. customdried
  7. dissolutionThe solid was dissolved in ethyl acetate
  8. washwashed with water, brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5d660ed3f61b4da8adce747ea3e8796b
Source dataset
uspto-grants-2011_08
Patent number
US07989463B2

Reaction notes

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