Triethylamine → 5-[(Z)-(5-fluoro-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 1243902Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.N1([C:17]([C:19]2[C:20]([CH3:27])=[C:21]([CH:25]=O)[NH:22][C:23]=2[CH3:24])=[O:18])C=CN=C1.[NH2:28][CH2:29][C@@H:30]([OH:38])[CH2:31][N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.C(N(CC)CC)C>C(#N)C.O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])/[C:5]/2=[CH:25]\[C:21]1[NH:22][C:23]([CH3:24])=[C:19]([C:17]([NH:28][CH2:29][C@@H:30]([OH:38])[CH2:31][N:32]2[CH2:33][CH2:34][O:35][CH2:36][CH2:37]2)=[O:18])[C:20]=1[CH3:27]

Participants

Conditions

Temperature: 60 °C

Procedure

A 0.25 L flask fitted with a thermometer, condenser, magnetic stirring, and nitrogen inlet was charged with 4.92 g 5-Fluorooxindole, 7.0 g 4-(1H-imidazol-1-ylcarbonyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde, 15.5 g (R)-1-Amino-3-(4-morpholinyl)-2-propanol, 9.78 g Triethylamine and 88 ml Tetrahydrofuran. The mixture was heated to 60° C. for 16.5 hours. The reaction was cooled to ambient temperature and filtered. The solids obtained were slurried (3) three successive times in acetonitrile at 11 ml/g, dried in vacuoto produce a yield of 3.6 g (25.25%) of 5-[(Z)-(5-fluoro-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.

Workup

customA 0.25 L flask fitted with a thermometer, condenser, magnetic stirring, and nitrogen inlet
temperatureThe reaction was cooled to ambient temperature
filtrationfiltered
customThe solids obtained
customdried in vacuoto

Sources & evidence

ORD record: ord-1476f8718fbf40229759cfd6fa67b934
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07119209B2

Reaction notes

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