Methanesulfonamide → 4-(bicyclo[4.1.0]heptan-3-ylmethoxy)-5-cyclopropyl-N-(cyclopropylsulfonyl)-2-fluorobenzamide

HRID 1849815Notes

Reaction equation

HRID 1849815 reaction equation
C(C1(COC2C(C3CC3)=CC(C(O)=O)=C(F)C=2)C2CC3CC(CC1C3)C2)#N.[CH:28]12[CH2:34][CH:33]1[CH2:32][CH2:31][CH:30]([CH2:35][O:36][C:37]1[C:45]([CH:46]3[CH2:48][CH2:47]3)=[CH:44][C:40]([C:41](O)=[O:42])=[C:39]([F:49])[CH:38]=1)[CH2:29]2.CS(N)(=O)=O.[CH:55]1([S:58]([NH2:61])(=[O:60])=[O:59])[CH2:57][CH2:56]1>>[CH:28]12[CH2:34][CH:33]1[CH2:32][CH2:31][CH:30]([CH2:35][O:36][C:37]1[C:45]([CH:46]3[CH2:48][CH2:47]3)=[CH:44][C:40]([C:41]([NH:61][S:58]([CH:55]3[CH2:57][CH2:56]3)(=[O:60])=[O:59])=[O:42])=[C:39]([F:49])[CH:38]=1)[CH2:29]2

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 15765418CyclopropanesulfonamideHCID 867036554-((2-Cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acidHCID 867036984-(Bicyclo[4.1.0]heptan-3-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid

Product 1

HCID 867036994-(bicyclo[4.1.0]heptan-3-ylmethoxy)-5-cyclopropyl-N-(cyclopropylsulfonyl)-2-fluorobenzamide

Procedure

Following the procedure as described in Example 332 Step 7 and making non-critical variations to replace 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid with 4-(bicyclo[4.1.0]heptan-3-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid and making variations as required to replace methanesulfonamide with cyclopropanesulfonamide, the title compound was obtained as a solid (0.043 g, 21%): 1H NMR (300 MHz, CDCl3) δ8.69 (d, J=16.4 Hz, 1H), 7.58 (d, J=9.1 Hz, 1H), 6.59 (d, J=14.5 Hz, 1H), 5.78-5.54 (m, 2H), 3.94-3.84 (m, 2H), 3.15-3.06 (m, 1H), 1.96-1.68 (m, 7H), 1.48-1.40 (m, 2H), 1.26-1.11 (m, 2H), 1.06-0.99 (m, 2H), 0.96-0.90 (m, 2H), 0.69-0.64 (m, 2H); MS (ES+) m/z 408.0 (M+1).

Sources & evidence

ORD record
ord-ee9d9fbbc9bb45f5842a6dc0f32c07ad
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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