Tetrahydrofuran → N-[3-formyl-2-[(2-naphthyloxy)methyl]-1-(4-oxo-4-{[(trifluoromethyl)sulfonyl]amino}butyl)-1H-indol-5-yl]cyclopentanecarboxamide

HRID 895767Notes

Reaction equation

[CH:1]1([C:6]([NH:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH2:18][CH2:19][CH2:20][C:21](O)=[O:22])[C:13]([CH2:24][O:25][C:26]2[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=2)=[C:12]3[CH:36]=[O:37])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.CCN=C=NCCCN(C)C.[F:49][C:50]([F:56])([F:55])[S:51]([NH2:54])(=[O:53])=[O:52].C1COCC1>CN(C1C=CN=CC=1)C.C(OCC)(=O)C.O>[CH:36]([C:12]1[C:11]2[C:15](=[CH:16][CH:17]=[C:9]([NH:8][C:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:7])[CH:10]=2)[N:14]([CH2:18][CH2:19][CH2:20][C:21](=[O:22])[NH:54][S:51]([C:50]([F:56])([F:55])[F:49])(=[O:53])=[O:52])[C:13]=1[CH2:24][O:25][C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=1)=[O:37]

Participants

Conditions

Temperature: 25 °C

Procedure

The acid (1 eq) from step 1 of Example 53A was weighed into a flask and to this was added EDCI (1.35 eq), DMAP (1.1 eq), trifluoromethanesulfonamide (1.05 eq) followed by anhydrous THF (0.026 M) and the reaction mixture was stirred at 25° C., 3 h. Worked up with ethyl acetate/water followed by washing the organic layer with 0.05N HCl, saturated bicarbonate and brine. Chromatographic purification then afforded the desired product in 94% yield.

Workup

washby washing the organic layer with 0.05N HCl, saturated bicarbonate and brine
customChromatographic purification

Sources & evidence

ORD record: ord-a2fa7d17ce3e4f529ebc7682cffd8036
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06916841B2

Reaction notes

Loading…