Diisopropylethylamine → HCID 86695077, compound

HRID 574351Notes

Reaction equation

[Br:1][C:2]1[CH:17]=[C:5]2[N:6]=[C:7]([CH3:16])[C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[C:9](Cl)[N:4]2[N:3]=1.Cl.[CH3:19][C:20]1([CH3:26])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.CCN(C(C)C)C(C)C>CN(C=O)C>[Br:1][C:2]1[CH:17]=[C:5]2[N:6]=[C:7]([CH3:16])[C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[C:9]([N:23]3[CH2:24][CH2:25][C:20]([CH3:26])([CH3:19])[CH2:21][CH2:22]3)[N:4]2[N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 2-(2-bromo-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (1.33 g, 4.18 mmol, 1 equiv) in DMF (14 mL) was added 4,4-dimethylpiperidine hydrochloride (0.75 g, 5.01 mmol, 1.2 equiv) and DIPEA (1.75 mL, 10.02 mmol, 2.4 equiv). The reaction was then heated in an oil bath at 60° C. Upon completion, the reaction was removed from heating, diluted with water, and extracted with EtOAc (×2). The combined EtOAc extracts were dried over Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel flash chromatography (0-100% EtOAc/hexane) to provide methyl 2-(2-bromo-7-(4,4-dimethylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate as an off white solid (1.50 g, 91%). 1H NMR (400 MHz, CDCl3) δ 6.53 (s, 1H), 3.80 (s, 2H), 3.77 (s, 3H), 3.41 (br. s., 4H), 2.51 (s, H), 1.54 (t, J=5.6 Hz, 4H), 1.09 (s, 6H); LCMS (ESI, M+1): 395.25.

Workup

customUpon completion, the reaction was removed
temperaturefrom heating
additiondiluted with water
extractionextracted with EtOAc (×2)
dry with materialThe combined EtOAc extracts were dried over Na2SO4
concentrationconcentrated in vacuo
customThe crude product was purified by silica gel flash chromatography (0-100% EtOAc/hexane)

Sources & evidence

ORD record: ord-9dd4fbbb379640f5bb3c35d06e48fe7b
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034882B2

Reaction notes

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