Diisopropylethylamine → HCID 58479440, compound

HRID 451212Notes

Reaction equation

[Cl:1][C:2]1[C:7]([NH:8][CH3:9])=[CH:6][N:5]=[C:4]2[N:10]([CH2:13][CH3:14])[N:11]=[CH:12][C:3]=12.CCN(C(C)C)C(C)C.[F:24][C:25]([F:43])([F:42])[C:26]1[CH:27]=[C:28]([C:36]([CH3:41])([CH3:40])[C:37](Cl)=[O:38])[CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1>C(Cl)Cl>[F:43][C:25]([F:24])([F:42])[C:26]1[CH:27]=[C:28]([C:36]([CH3:41])([CH3:40])[C:37]([N:8]([C:7]2[C:2]([Cl:1])=[C:3]3[CH:12]=[N:11][N:10]([CH2:13][CH3:14])[C:4]3=[N:5][CH:6]=2)[CH3:9])=[O:38])[CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of (4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-methyl-amine (2.24 g, 10.63 mmol) in CH2Cl2 (50 mL) was added iPr2NEt (3.69 mL, 21.20 mmol) and 2-(3,5-Bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride (described in J. Org. Chem, 2006, 71, 2000-2008, 4.38 g, 13.70 mmol). The reaction mixture was heated at 40° C. for 2 hours, diluted with CH2Cl2 (100 mL), and washed with H2O. The organic phase was dried over Na2SO4, concentrated under vacuo, and column chromatography (SiO2, EtOAc/Heptane 1/4) afforded 4.96 g (95%) of the title compound as a light yellow solid. ES-MS m/e: 493.2 (M+H+).

Workup

washwashed with H2O
dry with materialThe organic phase was dried over Na2SO4
concentrationconcentrated under vacuo, and column chromatography (SiO2, EtOAc/Heptane 1/4)

Sources & evidence

ORD record: ord-04a3dc2f5c684c87a17f0cd5454c3576
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487102B2

Reaction notes

Loading…