Methanesulfonamide → N-(azetidin-1-ylsulfonyl)-5-chloro-4-((2-cyanoadamantan-2-yl)-methoxy)-2-fluorobenzamide

HRID 1849777Notes

Reaction equation

HRID 1849777 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]([O:52][CH2:53][C:54]2([C:64]#[N:65])[CH:61]3[CH2:62][CH:57]4[CH2:58][CH:59]([CH2:63][CH:55]2[CH2:56]4)[CH2:60]3)=[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]([O:52][CH2:53][C:54]3([C:64]#[N:65])[CH:55]4[CH2:63][CH:59]5[CH2:58][CH:57]([CH2:62][CH:61]3[CH2:60]5)[CH2:56]4)=[CH:44][C:45]=2[F:51])(=[O:12])=[O:11])[CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 450805661-AzetidinesulfonamideHCID 867036554-((2-Cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acidHCID 867036585-Chloro-4-((2-cyanoadamantan-2-yl)methoxy)-2-fluorobenzoic acid

Product 1

HCID 86703660N-(azetidin-1-ylsulfonyl)-5-chloro-4-((2-cyanoadamantan-2-yl)-methoxy)-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 5-chloro-4-((2-cyanoadamantan-2-yl)methoxy)-2-fluorobenzoic acid, the title compound was obtained following purification by reverse-phase HPLC as a colorless powder (0.037 g, 18%): 1H NMR (300 MHz, DMSO-d6) δ 11.86 (br s, 1H), 7.78 (d, J=7.4 Hz, 1H), 7.41 (d, J=12.2 Hz, 1H), 4.54 (s, 2H), 4.02 (t, J=7.7, 7.7 Hz, 4H), 2.17-2.07 (m, 6H), 1.98-1.78 (m, 6H), 1.70-1.61 (m, 4H); MS (ES−) m/z 480.1, 482.1 (M−1).

Sources & evidence

ORD record
ord-ff605a3c80764de8bf51768190388036
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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