Methanesulfonamide → 4-(adamantan-1-ylmethoxy)-5-chloro-2-fluoro-N-((3-fluoroazetidin-1-yl)-sulfonyl)benzamide

HRID 1849555Notes

Reaction equation

HRID 1849555 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.[F:54][CH:55]1[CH2:58][N:57]([S:59]([NH2:62])(=[O:61])=[O:60])[CH2:56]1>>[C:26]12([CH2:36][O:37][C:38]3[C:46]([Cl:47])=[CH:45][C:41]([C:42]([NH:62][S:59]([N:57]4[CH2:58][CH:55]([F:54])[CH2:56]4)(=[O:61])=[O:60])=[O:43])=[C:40]([F:48])[CH:39]=3)[CH2:33][CH:32]3[CH2:31][CH:30]([CH2:29][CH:28]([CH2:34]3)[CH2:27]1)[CH2:35]2

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 703479833-Fluoroazetidine-1-sulfonamideHCID 867028594-(Adamantan-1-ylmethoxy)-5-chloro-2-fluorobenzoic acidHCID 867028614-(Adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid

Product 1

HCID 867028994-(adamantan-1-ylmethoxy)-5-chloro-2-fluoro-N-((3-fluoroazetidin-1-yl)-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 3-fluoroazetidine-1-sulfonamide, the title compound was obtained as colorless solid (0.15 g, 52%): 1H NMR (300 MHz, DMSO-d6) δ 12.02 (s, 1H), 7.77 (d, J=7.5 Hz, 1H), 7.25 (d, J=12.4 Hz, 1H), 5.49-5.43 (m, 0.5H), 5.30-5.24 (m, 0.5H), 4.45-4.32 (m, 2H), 4.26-4.13 (m, 2H), 3.73 (s, 2H), 1.99 (br s, 3H), 1.75-1.64 (m, 12H); MS (ES+) m/z 475.1, 477.1 (M+1); MS (ES−) m/z 473.2, 475.2 (M−1).

Sources & evidence

ORD record
ord-7c4fed68af174f479fc0ab69fcf84dfa
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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