Tetrahydrofuran → HCID 66993273, compound

HRID 381495Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C@@H:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23](=[O:46])/[CH:24]=[CH:25]/[C:26]3[CH:45]=[CH:44][C:29]([O:30][CH2:31][CH2:32][N:33]4C(=O)C5C(=CC=CC=5)C4=O)=[CH:28][CH:27]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1.C1COCC1.NN>CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C@@H:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23](=[O:46])/[CH:24]=[CH:25]/[C:26]3[CH:27]=[CH:28][C:29]([O:30][CH2:31][CH2:32][NH2:33])=[CH:44][CH:45]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of (E)-(R)-2-[2-(4-{3-[1-(2,3-dihydrobenzofuran-5-yl)-1,3,4,9-tetrahydro-β-carbolin-2-yl]-3-oxo-propenyl}-phenoxy)ethyl]isoindole-1,3-dione (0.85 g, 1.4 mmol) in 50 mL of MeOH:THF was added hydrazine (0.38 mL, 3 equiv., 35% in water). The resulting mixture was stirred at 45° C. for 4 hours. Evaporation in vacuo and flash chromatography with DCM:MeOH (80:20) as eluting solvent gave the title compound (0.17 g, 26%) as yellow powder.

Workup

customEvaporation in vacuo and flash chromatography with DCM:MeOH (80:20)
washas eluting solvent

Sources & evidence

ORD record: ord-7cf35347238444f58bdc36b945280c96
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06306870B1

Reaction notes

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