Diethyl Ether → HCID 59362930, compound

HRID 1668828Notes

Reaction equation

HRID 1668828 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].Cl.[F:27][C:28]1([F:34])[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C(N(C(C)C)CC)(C)C.CCOCC>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:31]4[CH2:32][CH2:33][C:28]([F:34])([F:27])[CH2:29][CH2:30]4)[N:17]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 81531DiisopropylethylamineHCID 27583514,4-Difluoropiperidine hydrochlorideHCID 59362943HCID 59362943, compound

Product 1

HCID 59362930HCID 59362930, compoundYield 77%

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 (0.36 g, 1 mmol), 4,4-difluoropiperidine hydrochloride (0.23 g, 1.5 mmol), diisopropylethylamine (0.5 mL, 3 mmol) in anhydrous isopropanol (10 mL) was heated to reflux for 48 hours. Thereafter, the mixture was cooled to a temperature in the range of 40° C. to 60° C. and concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed sequentially with water, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to yield a semi solid residue. Ether was added to the residue and the precipitates were filtered to afford the title compound as a white solid (0.34 g, 77% yield).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 48 hours
  3. temperatureThereafter, the mixture was cooled to a temperature in the range of 40° C. to 60° C.
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue was diluted with ethyl acetate
  6. washwashed sequentially with water, brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto yield a semi solid residue
  11. filtrationthe precipitates were filtered

Sources & evidence

ORD record
ord-79b0265735c94401a2a34578b0683aec
Source dataset
uspto-grants-2011_08
Patent number
US07989463B2

Reaction notes

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