Triethylamine → Sunitinib

HRID 1243900Notes

Reaction equation

N1([C:6]([C:8]2[C:9]([CH3:16])=[C:10]([CH:14]=O)[NH:11][C:12]=2[CH3:13])=[O:7])C=CN=C1.[CH2:17]([N:19]([CH2:23][CH3:24])[CH2:20][CH2:21][NH2:22])[CH3:18].[F:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[NH:31][C:30](=[O:35])[CH2:29]2.C(N(CC)CC)C>C(#N)C>[CH2:17]([N:19]([CH2:23][CH3:24])[CH2:20][CH2:21][NH:22][C:6]([C:8]1[C:9]([CH3:16])=[C:10](/[CH:14]=[C:29]2\[C:30](=[O:35])[NH:31][C:32]3[C:28]\2=[CH:27][C:26]([F:25])=[CH:34][CH:33]=3)[NH:11][C:12]=1[CH3:13])=[O:7])[CH3:18]

Participants

Conditions

Temperature: 60 °C

Procedure

4-(1H-imidazol-1-ylcarbonyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde (14.0 g), N,N-diethylethylenediamine (15.0 g), 5-fluorooxindole (9.86 g), triethylamine (27 ml), and acetonitrile (250 ml) were mixed and heated to 60° C. The black slurry was stirred for 18 h at 60° C. (needs mechanical stirrer). The resulting yellow slurry was cooled to room temperature, diluted with 100 ml acetonitrile, and filtered. The cake was washed with 3×100 ml acetonitrile and dried overnight at 50° C. under house vacuum. N-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide (21.7 g) was obtained with 85% yield.

Workup

temperatureThe resulting yellow slurry was cooled to room temperature
filtrationfiltered
washThe cake was washed with 3×100 ml acetonitrile
customdried overnight at 50° C. under house vacuum

Sources & evidence

ORD record: ord-ef4bef9c26054edcb8fc25b225a9416a
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07119209B2

Reaction notes

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