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

HRID 1849843Notes

Reaction equation

HRID 1849843 reaction equation
C(C1(COC2C(C3CC3)=CC(C(O)=O)=C(F)C=2)C2CC3CC(CC1C3)C2)#N.[C:28]12([CH2:38][O:39][C:40]3[C:48]([CH:49]4[CH2:52][CH2:51][CH2:50]4)=[CH:47][C:43]([C:44]([OH:46])=O)=[C:42]([F:53])[CH:41]=3)[CH2:37][CH:32]3[CH2:33][CH:34]([CH2:36][CH:30]([CH2:31]3)[CH2:29]1)[CH2:35]2.CS(N)(=O)=O.[N:59]1([S:63]([NH2:66])(=[O:65])=[O:64])[CH2:62][CH2:61][CH2:60]1>>[C:28]12([CH2:38][O:39][C:40]3[C:48]([CH:49]4[CH2:50][CH2:51][CH2:52]4)=[CH:47][C:43]([C:44]([NH:66][S:63]([N:59]4[CH2:62][CH2:61][CH2:60]4)(=[O:65])=[O:64])=[O:46])=[C:42]([F:53])[CH:41]=3)[CH2:29][CH:30]3[CH2:36][CH:34]([CH2:33][CH:32]([CH2:31]3)[CH2:37]1)[CH2:35]2

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 450805661-AzetidinesulfonamideHCID 867036554-((2-Cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acidHCID 867037284-(Adamantan-1-ylmethoxy)-5-cyclobutyl-2-fluorobenzoic acid

Product 1

HCID 867037304-(adamantan-1-ylmethoxy)-N-(azetidin-1-ylsulfonyl)-5-cyclobutyl-2-fluorobenzamide

Procedure

Following the procedure as described in Example 332 Step 7 and making non-critical variations to replace 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid with 4-(adamantan-1-ylmethoxy)-5-cyclobutyl-2-fluorobenzoic acid and to replace methanesulfonamide with azetidine-1-sulfonamide, the title compound was obtained as a colorless solid (0.043 g, 13%): 1H NMR (300 MHz, CDCl3) δ 8.66 (d, J=16.5 Hz, 1H), 7.88 (d, J=9.3 Hz, 1H), 6.54 (d, J=14.6 Hz, 1H), 4.24 (t, J=7.7 Hz, 4H), 3.69-3.58 (m, 1H), 3.49 (s, 2H), 2.39-1.99 (m, 10H), 1.87-1.64 (m, 13H); MS (ES−) m/z 475.2 (M−1).

Sources & evidence

ORD record
ord-aa22cc2c09284f709ba802415108c44f
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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