1-Azetidinesulfonamide → 4-(adamantan-1-ylmethoxy)-N-(azetidin-1-ylsulfonyl)-2-fluoro-5-vinylbenzamide

HRID 1849674Notes

Reaction equation

HRID 1849674 reaction equation
[C:1]12([CH2:11][O:12][C:13]3[C:21]([CH:22]4C[CH2:23]4)=[CH:20][C:16]([C:17]([OH:19])=O)=[C:15]([F:25])[CH:14]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C12(COC3C(C=C)=CC(C(O)=O)=C(F)C=3)CC3CC(CC(C3)C1)C2.C([CH:52]1[CH2:55][N:54]([S:56]([NH2:59])(=[O:58])=[O:57])[CH2:53]1)#N.N1(S(N)(=O)=O)CCC1>>[C:1]12([CH2:11][O:12][C:13]3[C:21]([CH:22]=[CH2:23])=[CH:20][C:16]([C:17]([NH:59][S:56]([N:54]4[CH2:55][CH2:52][CH2:53]4)(=[O:58])=[O:57])=[O:19])=[C:15]([F:25])[CH:14]=3)[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

5

Reactant 4

HCID 450805661-AzetidinesulfonamideHCID 867028614-(Adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acidHCID 867028964-(Adamantan-1-ylmethoxy)-2-fluoro-5-vinylbenzoic acidHCID 867035383-Cyanoazetidine-1-sulfonamide

Product 1

HCID 867035434-(adamantan-1-ylmethoxy)-N-(azetidin-1-ylsulfonyl)-2-fluoro-5-vinylbenzamide

Procedure

Following the procedure as described in Example 230 and making variations as required to replace 4-(adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid with 4-(adamantan-1-ylmethoxy)-2-fluoro-5-vinylbenzoic acid and 3-cyanoazetidine-1-sulfonamide with azetidine-1-sulfonamide, the title compound was obtained as colorless solid (0.13 g, 36%): 1H NMR (300 MHz, DMSO-d6) δ 11.75 (s, 1H), 7.81 (d, J=8.4 Hz, 1H), 7.04 (d, J=12.9 Hz, 1H), 6.91 (dd, J=11.3 Hz, 17.8 Hz, 1H), 5.93 (dd, J=1.0 Hz, 17.8 Hz, 1H), 5.37 (dd, J=1.0 Hz, 11.3 Hz, 1H), 4.06 (t, J=7.7 Hz, 4H), 3.67 (s, 2H), 2.23-2.12 (m, 2H), 2.00-1.99 (m, 3H), 1.75-1.64 (m, 12H); MS (ES+) m/z 449.1 (M+1); MS (ES−) m/z 447.3 (M−1).

Sources & evidence

ORD record
ord-f1241756a6af49379f7524d491b46b31
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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