Methanesulfonamide → HCID 86703744, compound

HRID 1849853Notes

Reaction equation

C(C1(COC2C(C3CC3)=CC(C(O)=O)=C(F)C=2)C2CC3CC(CC1C3)C2)#N.[CH:28]1([C:31]2[C:32]([O:41][CH2:42][CH:43]3[CH2:49][CH2:48][CH:47]4[CH:45]([C:46]4([F:51])[F:50])[CH2:44]3)=[CH:33][C:34]([F:40])=[C:35]([CH:39]=2)[C:36](O)=[O:37])[CH2:30][CH2:29]1.CS(N)(=O)=O.[CH:57]1([S:60]([NH2:63])(=[O:62])=[O:61])[CH2:59][CH2:58]1>>[CH:28]1([C:31]2[C:32]([O:41][CH2:42][CH:43]3[CH2:49][CH2:48][CH:47]4[CH:45]([C:46]4([F:50])[F:51])[CH2:44]3)=[CH:33][C:34]([F:40])=[C:35]([CH:39]=2)[C:36]([NH:63][S:60]([CH:57]2[CH2:59][CH2:58]2)(=[O:62])=[O:61])=[O:37])[CH2:30][CH2:29]1

Participants

Reactant 4

HCID 72879Methanesulfonamide

HCID 15765418Cyclopropanesulfonamide

HCID 867036554-((2-Cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid

HCID 86703743HCID 86703743, compound

Product 1

HCID 86703744HCID 86703744, compound

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 5-cyclopropyl-4-((7,7-difluorobicyclo[4.1.0]heptan-3-yl)methoxy)-2-fluorobenzoic acid and to replace methanesulfonamide with cyclopropanesulfonamide, the title compound was obtained as a colorless solid (0.012 g, 11%): 1H NMR (300 MHz, CDCl3) δ11.80 (br s, 1H), 7.10 (d, J=8.2 Hz, 1H), 7.02-6.87 (m, 1H), 4.14-3.78 (m, 2H), 3.12-2.50 (m, 2H), 2.42-2.05 (m, 2H), 2.05-1.27 (m, 5H), 1.28-1.14 (m, 2H), 1.15-0.95 (m, 4H), 0.95-0.74 (m, 2H), 0.70-0.54 (m, 2H); MS (ES+) m/z 444.1 (M+1).

Sources & evidence

ORD record: ord-86717c6c4d724dacb54c6f79326b58a5
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952169B2

Reaction notes

Loading…