Diisopropylethylamine → HCID 66847776, compound

HRID 1631404Notes

Reaction equation

Cl.[F:2][C:3]1[CH:4]=[C:5]([C@@H:9]2[NH:13][C@@:12]([CH2:15][OH:16])([CH3:14])[CH2:11][CH2:10]2)[CH:6]=[N:7][CH:8]=1.Cl[C:18]1[CH:23]=[CH:22][N:21]2[N:24]=[CH:25][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:20]2[N:19]=1.CCN(C(C)C)C(C)C>C(O)(C)C>[F:2][C:3]1[CH:4]=[C:5]([C@@H:9]2[N:13]([C:18]3[CH:23]=[CH:22][N:21]4[N:24]=[CH:25][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:20]4[N:19]=3)[C@@:12]([CH2:15][OH:16])([CH3:14])[CH2:11][CH2:10]2)[CH:6]=[N:7][CH:8]=1

Participants

Conditions

Temperature: 190 °C

Procedure

A sealed reaction vessel was charged with ((2S,5R)-5-(5-fluoropyridin-3-yl)-2-methylpyrrolidin-2-yl)methanol hydrochloride (0.135 g, 0.547 mmol), ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate (Preparation B, 0.136 g, 0.602 mmol), DIEA (0.124 mL, 0.711 mmol) and isopropyl alcohol (1 mL). The vessel was sealed and the mixture was heated at 190° C. for 48 hours. The reaction was cooled to ambient temperature and concentrated. The residue was purified by reverse phase column chromatography (0-50% acetonitrile/water) to afford ethyl 5-((2S,5R)-5-(5-fluoropyridin-3-yl)-2-(hydroxymethyl)-2-methylpyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (55 mg, 25% yield) as a viscous clear oil. MS (apci) m/z=400.1 (M+H).

Workup

customA sealed reaction vessel
customThe vessel was sealed
temperatureThe reaction was cooled to ambient temperature
concentrationconcentrated
customThe residue was purified by reverse phase column chromatography (0-50% acetonitrile/water)

Sources & evidence

ORD record: ord-f96c9d1d42b14906a945393f5ea3134d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791123B2

Reaction notes

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