Methanesulfonamide → 4-(adamantan-1-ylmethoxy)-N-(azetidin-1-ylsulfonyl)-2-fluoro-5-methylbenzamide

HRID 1849564Notes

Reaction equation

HRID 1849564 reaction equation
[C:1]12([CH2:11][O:12][C:13]3[C:21]([CH:22]4CC4)=[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)=CC(C(O)=O)=C(F)C=3)CC3CC(CC(C3)C1)C2.CS(N)(=O)=O.[N:54]1([S:58]([NH2:61])(=[O:60])=[O:59])[CH2:57][CH2:56][CH2:55]1>>[C:1]12([CH2:11][O:12][C:13]3[C:21]([CH3:22])=[CH:20][C:16]([C:17]([NH:61][S:58]([N:54]4[CH2:57][CH2:56][CH2:55]4)(=[O:60])=[O:59])=[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 867029084-(Adamantan-1-ylmethoxy)-2-fluoro-5-methylbenzoic acid

Product 1

HCID 867029094-(adamantan-1-ylmethoxy)-N-(azetidin-1-ylsulfonyl)-2-fluoro-5-methylbenzamide

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)-2-fluoro-5-methylbenzoic acid and methanesulfonamide with azetidine-1-sulfonamide, the title compound was obtained as colorless solid (0.06 g, 27%): 1H NMR (300 MHz, DMSO-d6) δ 11.59 (s, 1H), 7.48 (d, J=8.3 Hz, 1H), 6.93 (d, J=12.9 Hz, 1H), 4.04 (t, J=7.7 Hz, 4H), 3.62 (s, 2H), 2.19-2.14 (m, 5H), 1.99 (s, 3H), 1.75-1.66 (m, 12H); MS (ES+) m/z 437.2 (M+1); MS (ES−) m/z 435.2 (M−1).

Sources & evidence

ORD record
ord-2b6d8a3cf7a5449589a5ddcf3d09e05f
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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