Methanesulfonamide → N-(azetidin-1-ylsulfonyl)-4-(cyclopentylmethoxy)-5-cyclopropyl-2-fluorobenzamide

HRID 1849800Notes

Reaction equation

HRID 1849800 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([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](O)=[O:33])=[C:30]([F:40])[CH:29]=2)C2CC3C[CH:21]([CH2:25][CH:17]1C3)[CH2:22]2)#N.C1(COC2C(C3CC3)=CC(C(O)=O)=C(F)C=2)CCCC1>>[N:6]1([S:10]([NH:13][C:32](=[O:33])[C:31]2[CH:35]=[C:36]([CH:37]3[CH2:39][CH2:38]3)[C:28]([O:27][CH2:26][CH:16]3[CH2:22][CH2:21][CH2:25][CH2:17]3)=[CH:29][C:30]=2[F:40])(=[O:12])=[O:11])[CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 450805661-AzetidinesulfonamideHCID 867036214-(Cyclopentylmethoxy)-5-cyclopropyl-2-fluorobenzoic acidHCID 867036554-((2-Cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid

Product 1

HCID 86703684N-(azetidin-1-ylsulfonyl)-4-(cyclopentylmethoxy)-5-cyclopropyl-2-fluorobenzamide

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 4-(cyclopentylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid, the title compound was obtained following purification by reverse-phase HPLC as a colorless powder (0.037 g, 37%): 1H NMR (300 MHz, DMSO-d6) δ 11.60 (br s, 1H), 7.13 (d, J=8.3 Hz, 1H), 6.96 (d, J=13.0 Hz, 1H), 4.15-3.89 (m, 6H), 2.42-2.28 (m, 1H), 2.23-2.10 (m, 2H), 2.08-1.96 (m, 1H), 1.87-1.71 (m, 2H), 1.70-1.46 (m, 4H), 1.45-1.28 (m, 2H), 0.95-0.82 (m, 2H), 0.73-0.64 (m, 2H); MS (ES+) m/z 397.2 (M+1)

Sources & evidence

ORD record
ord-163ba300d63c4c0ab72f49f6cfcdefee
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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