Methanesulfonamide → N-(azetidin-1-ylsulfonyl)-5-chloro-2,4-difluorobenzamide

HRID 1849873Notes

Reaction equation

HRID 1849873 reaction equation
CS(N)(=O)=O.[N:6]1([S:10]([NH2:13])(=[O:12])=[O:11])[CH2:9][CH2:8][CH2:7]1.C(C1(COC2C(C3CC3)=CC(C(O)=O)=C(F)C=2)C2CC3CC(CC1C3)C2)#N.[Cl:41][C:42]1[C:43]([F:52])=[CH:44][C:45]([F:51])=[C:46]([CH:50]=1)[C:47](O)=[O:48]>>[N:6]1([S:10]([NH:13][C:47](=[O:48])[C:46]2[CH:50]=[C:42]([Cl:41])[C:43]([F:52])=[CH:44][C:45]=2[F:51])(=[O:12])=[O:11])[CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 148764175-Chloro-2,4-difluorobenzoic acidHCID 450805661-AzetidinesulfonamideHCID 867036554-((2-Cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid

Product 1

HCID 72548904N-(azetidin-1-ylsulfonyl)-5-chloro-2,4-difluorobenzamide

Procedure

Following the procedure as described in Example 332 Step 7 and making non-critical variations to replace methanesulfonamide with azetidine-1-sulfonamide and to replace 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid with 5-chloro-2,4-difluorobenzoic acid, the title compound was obtained as a colorless powder (7.0 g, 70%): 1H NMR (300 MHz, DMSO-d6) δ 12.07 (br s, 1H), 7.99 (t, J=7.6 Hz, 1H), 7.71 (t, J=9.8 Hz, 1H), 4.03 (t, J=7.7 Hz, 4H), 2.20-2.10 (m, 2H); MS (ES−) m/z 309.1, 311.1 (M−1).

Sources & evidence

ORD record
ord-db9fe9dbe6df47ca976f7506d78b4396
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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