Diisopropylethylamine → HCID 86664571, compound

HRID 1631344Notes

Reaction equation

Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[C@@H:10]1[NH:14][C:13]([CH3:16])([CH3:15])[CH2:12][CH2:11]1.C(N(C(C)C)CC)(C)C.Cl[C:27]1[CH:32]=[CH:31][N:30]2[N:33]=[CH:34][C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:29]2[N:28]=1>C(O)(C)C>[F:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[C@@H:10]1[N:14]([C:27]2[CH:32]=[CH:31][N:30]3[N:33]=[CH:34][C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:29]3[N:28]=2)[C:13]([CH3:16])([CH3:15])[CH2:12][CH2:11]1

Participants

Conditions

Temperature: 160 °C

Procedure

A sealed pressure tube was charged with (R)-5-(2,5-difluoro phenyl)-2,2-dimethylpyrrolidine HCl salt (300 mg, 1.21 mmol), diisopropylethylamine (423 μA, 2.42 mmol), ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate (273 mg, 1.21 mmol) and isopropanol (2.0 mL). The tube was sealed and the mixture was heated at 160° C. for 3 days. Additional ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate (273 mg, 1.21 mmol) was added and the reaction was heated at 160° C. 2 days. The reaction mixture was concentrated and the residue purified by reverse phase HPLC (eluting with 0-60% acetonitrile/H2O) to provide the title compound (136 mg, 28%) as a beige solid. MS (apci) m/z=401.1 (M+H).

Workup

customThe tube was sealed
temperaturethe reaction was heated at 160° C
custom2 days
concentrationThe reaction mixture was concentrated
customthe residue purified by reverse phase HPLC (eluting with 0-60% acetonitrile/H2O)

Sources & evidence

ORD record: ord-ca6dc0831b7440739bb820404c41abe2
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791123B2

Reaction notes

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