4-Morpholinopiperidine → (3Z)-3-({3,5-dimethyl-4-[(4-morpholin-4-ylpiperidin-1-yl)carbonyl]-1H-pyrrol-2-yl}methylene)-5-fluoro-1,3-dihydro-2H-indol-2-one

HRID 1243906Notes

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=[CH:2]1.[O:17]1[CH2:22][CH2:21][N:20]([CH:23]2[CH2:28]CNCC2)[CH2:19][CH2:18]1.[F:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[NH:35][C:34](=[O:39])[CH2:33]2>C1COCC1>[CH3:16][C:9]1[C:8]([C:6]([N:1]2[CH2:2][CH2:28][CH:23]([N:20]3[CH2:19][CH2:18][O:17][CH2:22][CH2:21]3)[CH2:4][CH2:5]2)=[O:7])=[C:12]([CH3:13])[NH:11][C:10]=1/[CH:14]=[C:33]1\[C:34](=[O:39])[NH:35][C:36]2[C:32]\1=[CH:31][C:30]([F:29])=[CH:38][CH:37]=2

Participants

Conditions

Temperature: 66 °C

Procedure

4-(1H-imidazol-1-ylcarbonyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde (11.3 g, 51.9 mmol), 4-morpholinopiperidine (15.0 g, 88.2 mmol), 5-fluorooxindole (7.84 g, 51.9 mmol), and THF (126 ml) were mixed and heated to 66° C. After stirring for 68 h at 66° C., the mixture was cooled to room temperature and filtered. The cake was washed with 4×20 ml THF and dried overnight at 70° C. under house vacuum. (3Z)-3-({3,5-dimethyl-4-[(4-morpholin-4-ylpiperidin-1-yl)carbonyl]-1H-pyrrol-2-yl}methylene)-5-fluoro-1,3-dihydro-2H-indol-2-one 16.09 g was obtained in 68% yield.

Workup

temperaturethe mixture was cooled to room temperature
filtrationfiltered
washThe cake was washed with 4×20 ml THF
customdried overnight at 70° C. under house vacuum

Sources & evidence

ORD record: ord-d423ba26eb3e458a84585b20e5f4ef07
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07119209B2

Reaction notes

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