Triethylamine → 5-[(Z)-(5-chloro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-N-[(2R)-2-hydroxy-3-morpholin-4-ylpropyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide

HRID 1243904Notes

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.[NH2:17][CH2:18][C@@H:19]([OH:27])[CH2:20][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.[Cl:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[NH:34][C:33](=[O:38])[CH2:32]2.C(N(CC)CC)C>C1COCC1>[Cl:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[NH:34][C:33](=[O:38])/[C:32]/2=[CH:14]\[C:10]1[NH:11][C:12]([CH3:13])=[C:8]([C:6]([NH:17][CH2:18][C@@H:19]([OH:27])[CH2:20][N:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)=[O:7])[C:9]=1[CH3:16]

Participants

Conditions

Temperature: 60 °C

Procedure

4-(1H-imidazol-1-ylcarbonyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde (7.0 g, 32.3 mmol), (2R)-1-amino-3-morpholin-4-ylpropan-2-ol (15.5 g, 96.9 mmol), 5-chlorooxindole (5.48 g, 32.6 mmol), triethylamine (14 ml), and THF (88 ml) were mixed and heated to 60° C. A red solution formed. After stirring for 16 h at 60° C., the yellow slurry was cooled to room temperature and filtered. The cake was washed with 2×50 ml of THF and dried overnight at 50° C. under house vacuum. 5-[(Z)-(5-chloro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-N-[(2R)-2-hydroxy-3-morpholin-4-ylpropyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide (4.36 g) was obtained in 29% yield.

Workup

customA red solution formed
temperaturethe yellow slurry was cooled to room temperature
filtrationfiltered
washThe cake was washed with 2×50 ml of THF
customdried overnight at 50° C. under house vacuum

Sources & evidence

ORD record: ord-2875ce27a7fc4610bbb0e29005c03221
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07119209B2

Reaction notes

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