Methanesulfonamide → N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-4-((4,4-difluorocyclohexyl)oxy)-2-fluorobenzamide

HRID 1849826Notes

Reaction equation

HRID 1849826 reaction equation
CS(N)(=O)=O.C1(S(N)(=O)=O)CC1.C(C1(COC2C(C3CC3)=CC(C(O)=O)=C(F)C=2)C2CC3CC(CC1C3)C2)#N.[CH:40]1([C:43]2[C:44]([O:53][CH:54]3[CH2:59][CH2:58][C:57]([F:61])([F:60])[CH2:56][CH2:55]3)=[CH:45][C:46]([F:52])=[C:47]([CH:51]=2)[C:48](O)=[O:49])[CH2:42][CH2:41]1.[N:62]1([S:66]([NH2:69])(=[O:68])=[O:67])[CH2:65][CH2:64][CH2:63]1>>[N:62]1([S:66]([NH:69][C:48](=[O:49])[C:47]2[CH:51]=[C:43]([CH:40]3[CH2:41][CH2:42]3)[C:44]([O:53][CH:54]3[CH2:59][CH2:58][C:57]([F:60])([F:61])[CH2:56][CH2:55]3)=[CH:45][C:46]=2[F:52])(=[O:68])=[O:67])[CH2:65][CH2:64][CH2:63]1

Participants

6

Reactant 5

HCID 72879Methanesulfonamide2×HCID 15765418CyclopropanesulfonamideHCID 450805661-AzetidinesulfonamideHCID 867036554-((2-Cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acidHCID 867037125-Cyclopropyl-4-((4,4-difluorocyclohexyl)oxy)-2-fluorobenzoic acid

Product 1

HCID 86703714N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-4-((4,4-difluorocyclohexyl)oxy)-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 5-cyclopropyl-4-((4,4-difluorocyclohexyl)oxy)-2-fluorobenzoic acid and to replace methanesulfonamide with azetidine-1-sulfonamide, the title compound was obtained as a colorless solid (0.092 g, 46%): 1H NMR (300 MHz, DMSO-d6) δ 11.58 (br s, 1H), 7.14-7.06 (m, 2H), 4.80 (br s, 1H), 4.00 (t, J=7.7, 7.7 Hz, 4H), 2.18-1.87 (m, 11H), 0.89-0.82 (m, 2H), 0.67-0.61 (m, 2H); 19F NMR (282 MHz, DMSO-d6) δ −92.0 (d, J=232 Hz, 1F), −98.5 (d, J=231 Hz, 1F), −112.7 (s, 1F); MS (ES−) m/z 431.1 (M−1).

Sources & evidence

ORD record
ord-b0133c052c6a49be8365146fe5da3f8f
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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