2-Morpholinoethylamine → 5-[(Z)-(5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-2,4-dimethyl-N-(2-morpholin-4-ylethyl)-1H-pyrrole-3-carboxamide

HRID 1243905Notes

Reaction equation

[N:1]1([C:6]([C:8]2[C:9]([CH3:16])=[C:10]([CH:14]=O)[NH:11][C:12]=2[CH3:13])=[O:7])[CH:5]=[CH:4][N:3]=[CH:2]1.NCCN1C[CH2:24][O:23][CH2:22][CH2:21]1.[F:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][C:31](=[O:36])[CH2:30]2>C1COCC1>[F:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][C:31](=[O:36])/[C:30]/2=[CH:14]\[C:10]1[NH:11][C:12]([CH3:13])=[C:8]([C:6]([NH:1][CH2:5][CH2:4][N:3]2[CH2:21][CH2:22][O:23][CH2:24][CH2:2]2)=[O:7])[C:9]=1[CH3:16]

Participants

Conditions

Temperature: 65 °C

Procedure

4-(1H-imidazol-1-ylcarbonyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde (5.0 g, 23.0 mmol), 4-(2-aminoethyl)morpholine (4.5 g, 34.6 mmol), 5-fluorooxindole (3.47 g, 23.0 mmol), and THF (80 ml) were mixed and heated to 65° C. After stirring for 24 h at 65° C., the mixture was cooled to room temperature and filtered. The cake was washed with 40 ml THF and dried overnight at 50° C. under house vacuum. 5-[(Z)-(5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-2,4-dimethyl-N-(2-morpholin-4-ylethyl)-1H-pyrrole-3-carboxamide (8.28 g) was obtained in 87% yield.

Workup

temperaturethe mixture was cooled to room temperature
filtrationfiltered
washThe cake was washed with 40 ml THF
customdried overnight at 50° C. under house vacuum

Sources & evidence

ORD record: ord-6feb8d33533b439fa701663a54b6a57e
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07119209B2

Reaction notes

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