Methanesulfonamide → N-{3-[4-(6-phenyl-8,9-dihydro-7H-benzocyclohepten-5-yl)-phenyl]-acryloyl}-methanesulfonamide

HRID 584576Notes

Reaction equation

HRID 584576 reaction equation
[C:1]1([C:7]2[CH2:13][CH2:12][CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[C:8]=2[C:18]2[CH:23]=[CH:22][C:21]([CH:24]=[CH:25][C:26]([OH:28])=O)=[CH:20][CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:29][S:30]([NH2:33])(=[O:32])=[O:31]>>[C:1]1([C:7]2[CH2:13][CH2:12][CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[C:8]=2[C:18]2[CH:23]=[CH:22][C:21]([CH:24]=[CH:25][C:26]([NH:33][S:30]([CH3:29])(=[O:32])=[O:31])=[O:28])=[CH:20][CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 72879MethanesulfonamideHCID 693150443-[4-(6-Phenyl-8,9-dihydro-7H-benzocyclohepten-5-yl)-phenyl]-acrylic acid

Product 1

HCID 69780805N-{3-[4-(6-phenyl-8,9-dihydro-7H-benzocyclohepten-5-yl)-phenyl]-acryloyl}-methanesulfonamide

Procedure

Prepared from the coupling of 2e and methylsulfonamide by the method described in Procedure 1, Method A. Yield (68%); 1H NMR (CDCl3) δ 7.66 (d, J=15.7 Hz, 1H), 7.18 (m, 10H), 6.95 (d, J=8.1 Hz, 2H), 6.84 (d, J=7.3 Hz, 1H), 6.28 (d, J=15.7 Hz, 1H), 3.36 (s, 3H), 2.82 (t, J=7.0 Hz, 2H), 2.41 (t, J=7.0 Hz, 2H), 2.19 (m, 2H); ESI m/z: 442 (M−H−, 100%).

Workup

  1. customYield (68%)

Sources & evidence

ORD record
ord-2947317f8e274e8791ec3879017c9830
Source dataset
uspto-grants-2005_08
Patent number
US06927224B2

Reaction notes

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