Methanesulfonamide → 5-cyclopropyl-4-((4,4-difluorocyclohexyl)-methoxy)-2-fluoro-N-((2-methoxyethyl)sulfonyl)benzamide

HRID 1849655Notes

Reaction equation

HRID 1849655 reaction equation
C1(C2C(OCC3(C(F)(F)F)CCCCC3)=CC(F)=C(C=2)C(O)=O)CC1.[CH:26]1([C:29]2[C:30]([O:39][CH2:40][CH:41]3[CH2:46][CH2:45][C:44]([F:48])([F:47])[CH2:43][CH2:42]3)=[CH:31][C:32]([F:38])=[C:33]([CH:37]=2)[C:34]([OH:36])=O)[CH2:28][CH2:27]1.CS(N)(=O)=O.[CH3:54][O:55][CH2:56][CH2:57][S:58]([NH2:61])(=[O:60])=[O:59]>>[CH:26]1([C:29]2[C:30]([O:39][CH2:40][CH:41]3[CH2:42][CH2:43][C:44]([F:47])([F:48])[CH2:45][CH2:46]3)=[CH:31][C:32]([F:38])=[C:33]([CH:37]=2)[C:34]([NH:61][S:58]([CH2:57][CH2:56][O:55][CH3:54])(=[O:60])=[O:59])=[O:36])[CH2:27][CH2:28]1

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 189515062-Methoxyethane-1-sulfonamideHCID 867034505-Cyclopropyl-2-fluoro-4-((1-(trifluoromethyl)-cyclohexyl)methoxy)benzoic acidHCID 867035175-Cyclopropyl-4-((4,4-difluorocyclohexyl)-methoxy)-2-fluorobenzoic acid

Product 1

HCID 867035195-cyclopropyl-4-((4,4-difluorocyclohexyl)-methoxy)-2-fluoro-N-((2-methoxyethyl)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 5-cyclopropyl-4-((4,4-difluorocyclohexyl)-methoxy)-2-fluorobenzoic acid and to replace methanesulfonamide with 2-methoxyethanesulfonamide, the title compound was obtained (0.072 g, 26%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ8.70-8.58 (m, 1H), 7.63-7.53 (m, 1H), 6.63-6.51 (m, 1H), 3.93-3.83 (m, 4H), 3.83-3.75 (m, 2H), 3.31 (s, 3H), 2.27-2.09 (m, 2H), 2.08-1.66 (m, 6H), 1.61-1.42 (m, 2H), 0.99-0.88 (m, 2H), 0.71-0.60 (m, 2H); MS (ES+) m/z 450.0 (M+1).

Sources & evidence

ORD record
ord-4d472e443d7846058db164893c0fd417
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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