Methanesulfonamide → 4-(bicyclo[4.1.0]heptan-1-ylmethoxy)-5-cyclopropyl-2-fluoro-N-((2-methoxyethyl)sulfonyl)benzamide

HRID 1849786Notes

Reaction equation

HRID 1849786 reaction equation
CS(N)(=O)=O.[CH3:6][O:7][CH2:8][CH2:9][S:10]([NH2:13])(=[O:12])=[O:11].C([C:16]1([CH2:26][O:27][C:28]2[C:36]([CH:37]3[CH2:39][CH2:38]3)=[CH:35][C:31]([C:32]([OH:34])=O)=[C:30]([F:40])[CH:29]=2)[CH:23]2[CH2:24][CH:19]3CC(C[CH:17]1[CH2:18]3)[CH2:22]2)#N.C12(COC3C(C4CC4)=CC(C(O)=O)=C(F)C=3)CC1CCCC2>>[C:16]12([CH2:26][O:27][C:28]3[C:36]([CH:37]4[CH2:38][CH2:39]4)=[CH:35][C:31]([C:32]([NH:13][S:10]([CH2:9][CH2:8][O:7][CH3:6])(=[O:12])=[O:11])=[O:34])=[C:30]([F:40])[CH:29]=3)[CH2:22][CH:23]1[CH2:24][CH2:19][CH2:18][CH2:17]2

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 189515062-Methoxyethane-1-sulfonamideHCID 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 867036684-(bicyclo[4.1.0]heptan-1-ylmethoxy)-5-cyclopropyl-2-fluoro-N-((2-methoxyethyl)sulfonyl)benzamide

Procedure

Following the procedure as described in Example 332 Step 7 and making non-critical variations to replace methanesulfonamide with 2-methoxyethanesulfonamide 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 (0.035 g, 39%): 1H NMR (300 MHz, DMSO-d6) δ 11.87 (br s, 1H), 7.11 (d, J=8.3 Hz, 1H), 6.86 (d, J=13.1 Hz, 1H), 3.72 (s, 3H), 3.36-3.31 (m, 4H), 3.22-3.19 (m, 2H), 2.12-1.96 (m, 1H), 1.95-1.67 (m, 3H), 1.66-1.50 (m, 1H), 1.44-1.04 (m, 4H), 1.02-0.82 (m, 3H), 0.76-0.55 (m, 3H), 0.43-0.30 (m, 1H); MS (ES+) m/z 426.1 (M+1)

Sources & evidence

ORD record
ord-3a6f57154f884ffdb2db8d6b315d319f
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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