Methanesulfonamide → 4-(bicyclo[4.1.0]heptan-1-ylmethoxy)-5-cyclopropyl-N-(cyclopropylsulfonyl)-2-fluorobenzamide

HRID 1849785Notes

Reaction equation

HRID 1849785 reaction equation
CS(N)(=O)=O.[CH:6]1([S:9]([NH2:12])(=[O:11])=[O:10])[CH2:8][CH2:7]1.C([C:15]1([CH2:25][O:26][C:27]2[C:35]([CH:36]3[CH2:38][CH2:37]3)=[CH:34][C:30]([C:31]([OH:33])=O)=[C:29]([F:39])[CH:28]=2)[CH:22]2[CH2:23][CH:18]3CC(C[CH:16]1[CH2:17]3)[CH2:21]2)#N.C12(COC3C(C4CC4)=CC(C(O)=O)=C(F)C=3)CC1CCCC2>>[C:15]12([CH2:25][O:26][C:27]3[C:35]([CH:36]4[CH2:37][CH2:38]4)=[CH:34][C:30]([C:31]([NH:12][S:9]([CH:6]4[CH2:8][CH2:7]4)(=[O:11])=[O:10])=[O:33])=[C:29]([F:39])[CH:28]=3)[CH2:21][CH:22]1[CH2:23][CH2:18][CH2:17][CH2:16]2

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 15765418CyclopropanesulfonamideHCID 867036554-((2-Cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acidHCID 867036674-(Bicyclo[4.1.0]heptan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid

Product 1

HCID 725463854-(bicyclo[4.1.0]heptan-1-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 methanesulfonamide with cyclopropanesulfonamide and to replace 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid with 4-(bicyclo[4.1.0]heptan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid, the title compound was obtained following purification by reverse-phase HPLC as a colorless powder (0.037 g, 37%): 1H NMR (300 MHz, DMSO-d6) δ 11.81 (br s, 1H), 7.13 (d, J=8.3 Hz, 1H), 6.87 (d, J=13.1 Hz, 1H), 3.92-3.73 (m, 2H), 3.13-3.01 (m, 1H), 2.10-1.96 (m, 1H), 1.95-1.49 (m, 4H), 1.40-1.03 (m, 8H), 1.03-0.93 (m, 1H), 0.94-0.82 (m, 2H), 0.77-0.59 (m, 3H), 0.41-0.32 (m, 1H); MS (ES+) m/z 408.1 (M+1)

Sources & evidence

ORD record
ord-f8c2fc8a98124ab6b189e70875d6191f
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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