Methanesulfonamide → 4-(adamantan-1-ylmethoxy)-N-(azetidin-1-ylsulfonyl)-5-ethyl-2-fluorobenzamide

HRID 1849554Notes

Reaction equation

HRID 1849554 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(CC)=CC(C(O)=O)=C(F)C=3)CC3CC(CC(C3)C1)C2.CS(N)(=O)=O.[N:55]1([S:59]([NH2:62])(=[O:61])=[O:60])[CH2:58][CH2:57][CH2:56]1>>[C:1]12([CH2:11][O:12][C:13]3[C:21]([CH2:22][CH3:23])=[CH:20][C:16]([C:17]([NH:62][S:59]([N:55]4[CH2:58][CH2:57][CH2:56]4)(=[O:61])=[O:60])=[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 72879MethanesulfonamideHCID 450805661-AzetidinesulfonamideHCID 867028614-(Adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acidHCID 867028974-(Adamantan-1-ylmethoxy)-5-ethyl-2-fluorobenzoic acid

Product 1

HCID 867028984-(adamantan-1-ylmethoxy)-N-(azetidin-1-ylsulfonyl)-5-ethyl-2-fluorobenzamide

Procedure

Following the procedure as described in Example 50 step 5 and making variations as required to replace 4-(adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid with 4-(adamantan-1-ylmethoxy)-5-ethyl-2-fluorobenzoic acid and methanesulfonamide with azetidine-1-sulfonamide, the title compound was obtained as colorless solid (0.16 g, 59%): 1H NMR (300 MHz, DMSO-d6) δ 11.60 (s, 1H), 7.46 (d, J=8.5 Hz, 1H), 6.94 (d, J=13.0 Hz, 1H), 4.08-4.01 (m, 4H), 3.62 (s, 2H), 2.59 (q, J=7.5 Hz, 2H), 2.22-2.12 (m, 2H), 1.99 (br s, 3H), 1.75-1.64 (m, 12H), 1.15 (t, J=7.5 Hz, 3H); MS (ES+) m/z 451.2 (M+1); MS (ES−) m/z 449.3 (M−1).

Sources & evidence

ORD record
ord-e576d5b4aa784e1781c956744a99c745
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

Loading…