Triethylamine → HCID 178454990, compound

HRID 2405898Notes

Reaction equation

HRID 2405898 reaction equation
[C:1]([Si:5]([C:8]1[C:13]([F:14])=[C:12]([F:15])[N:11]=[C:10]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[N:22][C:23]=3Cl)[NH:18][N:17]=2)[C:9]=1[F:26])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C>CCOC(C)=O>[Si:5]([C:8]1[C:13]([F:14])=[C:12]([F:15])[N:11]=[C:10]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[N:22][CH:23]=3)[NH:18][N:17]=2)[C:9]=1[F:26])([C:1]([CH3:3])([CH3:4])[CH3:2])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 178454991HCID 178454991, compound

Product 1

HCID 178454990HCID 178454990, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl-[2-(4-chloro-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-3,5,6-trifluoro-4-pyridyl]-dimethyl-silane (398 mg, 1.00 mmol), triethylamine (100.7 mg, 138.7 μL, 0.9953 mmol) in EtOAc (19 mL) was subjected to hydrogenation using H-cube apparatus. The following conditions were used to transform the starting material to subtitle product; 1×500 μL injection at 100 μL/min @ 70° C. followed by 4×4000 μL injection of reagent solution run at 150 μL/min @ 70° C. The product fractions were combined, diluted with EtOAc, washed with water (3×), brine, dried (MgSO4), filtered and concentrated in vacuo to give the sub title product as an orange solid (172 mg, 43.2% Yield). H1 NMR (400 MHz, DMSO) δ 14.59 (1H, s), 9.66 (1H, s), 9.10 (1H, m), 0.96 (9H, s) and 0.48 (6H, s).

Sources & evidence

ORD record
ord-493835fb4ea3433ea12feb02a8473dad
Source dataset
uspto-grants-2014_08
Patent number
US08809335B2

Reaction notes

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