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

HRID 1849842Notes

Reaction equation

HRID 1849842 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](O)=[O:45])=[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.[CH:59]1([S:62]([NH2:65])(=[O:64])=[O:63])[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:65][S:62]([CH:59]4[CH2:61][CH2:60]4)(=[O:64])=[O:63])=[O:45])=[C:42]([F:53])[CH:41]=3)[CH2:35][CH:34]3[CH2:36][CH:30]([CH2:31][CH:32]([CH2:33]3)[CH2:37]1)[CH2:29]2

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 15765418CyclopropanesulfonamideHCID 867036554-((2-Cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acidHCID 867037284-(Adamantan-1-ylmethoxy)-5-cyclobutyl-2-fluorobenzoic acid

Product 1

HCID 867037294-(adamantan-1-ylmethoxy)-5-cyclobutyl-N-(cyclopropylsulfonyl)-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 cyclopropanesulfonamide, the title compound was obtained as a colorless solid (0.090 g, 35%): 1H NMR (300 MHz, CDCl3) δ 8.69 (d, J=16.3 Hz, 1H), 7.87 (d, J=9.3 Hz, 1H), 6.53 (d, J=14.71H), 3.69-3.56 (m, 1H), 3.49 (s, 2H), 3.15-3.06 (m, 1H), 2.39-2.29 (m, 2H), 2.18-1.98 (m, 6H), 1.87-1.65 (m, 13H), 1.48-1.42 (m, 2H), 1.17-1.10 (m, 2H); MS (ES−) m/z 460.2 (M−1).

Sources & evidence

ORD record
ord-5a3caab348394724ae9279cb17a8e4f0
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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