Methanesulfonamide → 4-(adamantan-1-ylmethoxy)-5-chloro-2-fluoro-N-((2-methoxyethyl)sulfonyl)benzamide

HRID 1849558Notes

Reaction equation

HRID 1849558 reaction equation
C12(COC3C(C4CC4)=CC(C(O)=O)=C(F)C=3)CC3CC(CC(C3)C1)C2.[C:26]12([CH2:36][O:37][C:38]3[C:46]([Cl:47])=[CH:45][C:41]([C:42](O)=[O:43])=[C:40]([F:48])[CH:39]=3)[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[CH2:27]1)[CH2:33]2.CS(N)(=O)=O.[CH3:54][O:55][CH2:56][CH2:57][S:58]([NH2:61])(=[O:60])=[O:59]>>[C:26]12([CH2:36][O:37][C:38]3[C:46]([Cl:47])=[CH:45][C:41]([C:42]([NH:61][S:58]([CH2:57][CH2:56][O:55][CH3:54])(=[O:60])=[O:59])=[O:43])=[C:40]([F:48])[CH:39]=3)[CH2:27][CH:28]3[CH2:29][CH:30]([CH2:31][CH:32]([CH2:34]3)[CH2:33]1)[CH2:35]2

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 189515062-Methoxyethane-1-sulfonamideHCID 867028594-(Adamantan-1-ylmethoxy)-5-chloro-2-fluorobenzoic acidHCID 867028614-(Adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid

Product 1

HCID 867029034-(adamantan-1-ylmethoxy)-5-chloro-2-fluoro-N-((2-methoxyethyl)sulfonyl)benzamide

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-chloro-2-fluorobenzoic acid and methanesulfonamide with 2-methoxyethane-1-sulfonamide, the title compound was obtained as a colorless solid (0.05 g, 9%): 1H NMR (300 MHz, CDCl3) δ 8.68-8.54 (m, 1H), 8.13-8.03 (m, 1H), 6.74-6.62 (m, 1H), 3.91-3.74 (m, 4H), 3.59 (s, 2H), 3.31 (s, 3H), 2.05 (s, 3H), 1.85-1.64 (m, 12H); MS (ES−) m/z 458.3 (M−1), 460.3 (M−1).

Sources & evidence

ORD record
ord-98662afbd7af436caec271458960883a
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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