Methanesulfonamide → 4-(cyclohexylmethoxy)-5-cyclopropyl-2-fluoro-N-((3-fluoroazetidin-1-yl)sulfonyl)benzamide

HRID 1849630Notes

Reaction equation

HRID 1849630 reaction equation
[CH:1]1([C:4]2[C:5]([O:14][CH2:15][C:16]3(C(F)(F)F)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:6][C:7]([F:13])=[C:8]([CH:12]=2)[C:9]([OH:11])=O)[CH2:3][CH2:2]1.C1(COC2C(C3CC3)=CC(C(O)=O)=C(F)C=2)CCCCC1.CS(N)(=O)=O.[F:52][CH:53]1[CH2:56][N:55]([S:57]([NH2:60])(=[O:59])=[O:58])[CH2:54]1>>[CH:16]1([CH2:15][O:14][C:5]2[C:4]([CH:1]3[CH2:3][CH2:2]3)=[CH:12][C:8]([C:9]([NH:60][S:57]([N:55]3[CH2:56][CH:53]([F:52])[CH2:54]3)(=[O:59])=[O:58])=[O:11])=[C:7]([F:13])[CH:6]=2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 703479833-Fluoroazetidine-1-sulfonamideHCID 867034505-Cyclopropyl-2-fluoro-4-((1-(trifluoromethyl)-cyclohexyl)methoxy)benzoic acidHCID 867034874-(Cyclohexylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid

Product 1

HCID 867034884-(cyclohexylmethoxy)-5-cyclopropyl-2-fluoro-N-((3-fluoroazetidin-1-yl)sulfonyl)benzamide

Procedure

Following the procedure as described in Example 158 step 5, and making variations as required to replace 5-cyclopropyl-2-fluoro-4-((1-(trifluoromethyl)-cyclohexyl)methoxy)benzoic acid with 4-(cyclohexylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid and to replace methanesulfonamide with 3-fluoroazetidine-1-sulfonamide, the title compound was obtained (0.09 g, 35%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ8.80-8.64 (m, 1H), 7.62-7.52 (m, 1H), 6.64-6.52 (m, 1H), 5.45-5.12 (m, 1H), 4.59-4.31 (m, 4H), 3.89-3.76 (m, 2H), 2.13-1.99 (m, 1H), 1.96-1.68 (m, 6H), 1.42-1.03 (m, 5H), 1.00-0.89 (m, 2H), 0.72-0.62 (m, 2H); MS (ES+) m/z 429.2 (M+1).

Sources & evidence

ORD record
ord-ed644731c3f9490ab4e24814db84fd7f
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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