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

HRID 1849648Notes

Reaction equation

HRID 1849648 reaction equation
C1(C2C(OCC3(C(F)(F)F)CCCCC3)=CC(F)=C(C=2)C(O)=O)CC1.[CH:26]12[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[CH:27]1[CH2:36][O:37][C:38]1[C:46]([CH:47]3[CH2:49][CH2:48]3)=[CH:45][C:41]([C:42](O)=[O:43])=[C:40]([F:50])[CH:39]=1)[CH2:33]2.CS(N)(=O)=O.[N:56]1([S:60]([NH2:63])(=[O:62])=[O:61])[CH2:59][CH2:58][CH2:57]1>>[CH:26]12[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[CH:27]1[CH2:36][O:37][C:38]1[C:46]([CH:47]3[CH2:48][CH2:49]3)=[CH:45][C:41]([C:42]([NH:63][S:60]([N:56]3[CH2:59][CH2:58][CH2:57]3)(=[O:62])=[O:61])=[O:43])=[C:40]([F:50])[CH:39]=1)[CH2:33]2

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 450805661-AzetidinesulfonamideHCID 867034505-Cyclopropyl-2-fluoro-4-((1-(trifluoromethyl)-cyclohexyl)methoxy)benzoic acidHCID 867035094-(Adamantan-2-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid

Product 1

HCID 867035114-(adamantan-2-ylmethoxy)-N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-2-fluorobenzamide

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-(adamantan-2-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid and to replace methanesulfonamide with azetidine-1-sulfonamide, the title compound was obtained (0.07 g, 26%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ8.72-8.62 (m, 1H), 7.60-7.54 (m, 1H), 6.67-6.59 (m, 1H), 4.31-4.20 (m, 4H), 4.14-4.07 (m, 2H), 2.36-2.20 (m, 3H), 2.08-1.75 (m, 13H), 1.70-1.60 (m, 2H), 0.97-0.89 (m, 2H), 0.71-0.63 (m, 2H); MS (ES−) m/z 461.3 (M−1).

Sources & evidence

ORD record
ord-22d86365d084481198fad523496a3cb7
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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