Methanesulfonamide → N-(azetidin-1-ylsulfonyl)-4-(cyclohexylmethoxy)-5-cyclopropyl-2-fluorobenzamide

HRID 1849633Notes

Reaction equation

HRID 1849633 reaction equation
C1(C2C(OCC3(C(F)(F)F)CCCCC3)=CC(F)=C(C=2)C(O)=O)CC1.[CH:26]1([CH2:32][O:33][C:34]2[C:42]([CH:43]3[CH2:45][CH2:44]3)=[CH:41][C:37]([C:38]([OH:40])=O)=[C:36]([F:46])[CH:35]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.CS(N)(=O)=O.[N:52]1([S:56]([NH2:59])(=[O:58])=[O:57])[CH2:55][CH2:54][CH2:53]1>>[N:52]1([S:56]([NH:59][C:38](=[O:40])[C:37]2[CH:41]=[C:42]([CH:43]3[CH2:45][CH2:44]3)[C:34]([O:33][CH2:32][CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]3)=[CH:35][C:36]=2[F:46])(=[O:58])=[O:57])[CH2:55][CH2:54][CH2:53]1

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 450805661-AzetidinesulfonamideHCID 867034505-Cyclopropyl-2-fluoro-4-((1-(trifluoromethyl)-cyclohexyl)methoxy)benzoic acidHCID 867034874-(Cyclohexylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid

Product 1

HCID 86703492N-(azetidin-1-ylsulfonyl)-4-(cyclohexylmethoxy)-5-cyclopropyl-2-fluorobenzamide

Procedure

Following the procedure as described in preparation of 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 azetidine-1-sulfonamide, the title compound was obtained (0.13 g, 47%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 8.71-8.61 (m, 1H), 7.62-7.55 (m, 1H), 6.62-6.51 (m, 1H), 4.30-4.18 (m, 4H), 3.86-3.76 (m, 2H), 2.34-2.20 (m, 2H), 2.13-2.00 (m, 1H), 1.96-1.67 (m, 6H), 1.41-1.02 (m, 5H), 0.99-0.87 (m, 2H), 0.72-0.61 (m, 2H); MS (ES−) m/z 409.3 (M−1).

Workup

  1. customas described in preparation of Example 158 step 5

Sources & evidence

ORD record
ord-bc77f9a5d3f046d6b385efc36231d32a
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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