Diisopropylethylamine → N-[1-Benzyl-4-(4-fluoro-2-methyl-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-isobutyramide

HRID 451218Notes

Reaction equation

HRID 451218 reaction equation
[CH2:1]([N:8]1[C:12]2=[N:13][CH:14]=[C:15]([NH:25][CH3:26])[C:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[CH3:24])=[C:11]2[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[F:36][C:37]([F:55])([F:54])[C:38]1[CH:39]=[C:40]([C:48]([CH3:53])([CH3:52])[C:49](Cl)=[O:50])[CH:41]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:43]=1>C(Cl)Cl>[CH2:1]([N:8]1[C:12]2=[N:13][CH:14]=[C:15]([N:25]([CH3:26])[C:49](=[O:50])[C:48]([C:40]3[CH:39]=[C:38]([C:37]([F:55])([F:54])[F:36])[CH:43]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:41]=3)([CH3:53])[CH3:52])[C:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[CH3:24])=[C:11]2[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 112671412-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chlorideHCID 67441403[1-Benzyl-4-(4-fluoro-2-methyl-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-methyl-amine

Product 1

HCID 53496314N-[1-Benzyl-4-(4-fluoro-2-methyl-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-isobutyramideYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of [1-benzyl-4-(4-fluoro-2-methyl-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-methyl-amine (2.125 g, 6.13 mmol) in CH2Cl2 (30 mL) was added iPr2NEt (2.14 mL, 12.3 mmol) and 2-(3,5-Bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride (described in J. Org. Chem, 2006, 71, 2000-2008, 2.93 g, 9.20 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 3.2 g (83%) of the title compound as a white foam. ES-MS m/e: 629.2 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-b48a4a7741634012a19bc94a59307f93
Source dataset
uspto-grants-2013_07
Patent number
US08487102B2

Reaction notes

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