Methanesulfonamide → 5-cyclopropyl-4-((7,7-difluorobicyclo[4.1.0]heptan-1-yl)methoxy)-2-fluoro-N-((2-methoxyethyl)sulfonyl)benzamide

HRID 1849795Notes

Reaction equation

HRID 1849795 reaction equation
CS(N)(=O)=O.[CH3:6][O:7][CH2:8][CH2:9][S:10]([NH2:13])(=[O:12])=[O:11].C(C1(COC2C(C3CC3)=CC(C(O)=O)=C(F)C=2)C2CC3CC(CC1C3)C2)#N.[CH:41]1([C:44]2[C:45]([O:54][CH2:55][C:56]34[C:62]([F:64])([F:63])[CH:61]3[CH2:60][CH2:59][CH2:58][CH2:57]4)=[CH:46][C:47]([F:53])=[C:48]([CH:52]=2)[C:49](O)=[O:50])[CH2:43][CH2:42]1>>[CH:41]1([C:44]2[C:45]([O:54][CH2:55][C:56]34[C:62]([F:64])([F:63])[CH:61]3[CH2:60][CH2:59][CH2:58][CH2:57]4)=[CH:46][C:47]([F:53])=[C:48]([CH:52]=2)[C:49]([NH:13][S:10]([CH2:9][CH2:8][O:7][CH3:6])(=[O:12])=[O:11])=[O:50])[CH2:43][CH2:42]1

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 189515062-Methoxyethane-1-sulfonamideHCID 867036554-((2-Cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acidHCID 867036765-Cyclopropyl-4-((7,7-difluorobicyclo[4.1.0]heptan-1-yl)methoxy)-2-fluorobenzoic acid

Product 1

HCID 867036785-cyclopropyl-4-((7,7-difluorobicyclo[4.1.0]heptan-1-yl)methoxy)-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 5-cyclopropyl-4-((7,7-difluorobicyclo[4.1.0]heptan-1-yl)methoxy)-2-fluorobenzoic acid, the title compound was obtained following purification by reverse-phase HPLC as a colorless powder (0.045 g, 74%): 1H NMR (300 MHz, DMSO-d6) δ 11.92 (br s, 1H), 7.13 (d, J=8.3 Hz, 1H), 6.94 (d, J=12.8 Hz, 1H), 4.23-3.92 (m, 2H), 3.72 (s, 3H), 3.39-3.28 (m, 2H), 3.23-3.18 (m, 2H), 2.08-1.58 (m, 6H), 1.38-1.16 (m, 4H), 0.96-0.84 (m, 2H), 0.74-0.64 (m, 2H); MS (ES+) m/z 463.0 (M+1)

Sources & evidence

ORD record
ord-6e90819a742d446cb517e58e3127375b
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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