Methanesulfonamide → 4-(adamantan-1-ylmethoxy)-5-chloro-2-fluoro-N-((1-methyl-1H-imidazol-4-yl)sulfonyl)benzamide

HRID 1849572Notes

Reaction equation

HRID 1849572 reaction equation
C12(COC3C(C4CC4)=CC(C(O)=O)=C(F)C=3)CC3CC(CC(C3)C1)C2.[C:26]12([CH2:36][O:37][C:38]3[C:46]([Cl:47])=[CH:45][C:41]([C:42]([OH:44])=O)=[C:40]([F:48])[CH:39]=3)[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[CH2:27]1)[CH2:33]2.CS(N)(=O)=O.[CH3:54][N:55]1[CH:59]=[C:58]([S:60]([NH2:63])(=[O:62])=[O:61])[N:57]=[CH:56]1>>[C:26]12([CH2:36][O:37][C:38]3[C:46]([Cl:47])=[CH:45][C:41]([C:42]([NH:63][S:60]([C:58]4[N:57]=[CH:56][N:55]([CH3:54])[CH:59]=4)(=[O:62])=[O:61])=[O:44])=[C:40]([F:48])[CH:39]=3)[CH2:33][CH:32]3[CH2:31][CH:30]([CH2:29][CH:28]([CH2:34]3)[CH2:27]1)[CH2:35]2

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 27368851-methyl-1H-imidazole-4-sulfonamideHCID 867028594-(Adamantan-1-ylmethoxy)-5-chloro-2-fluorobenzoic acidHCID 867028614-(Adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid

Product 1

HCID 867029184-(adamantan-1-ylmethoxy)-5-chloro-2-fluoro-N-((1-methyl-1H-imidazol-4-yl)sulfonyl)benzamide

Procedure

Following the procedure as described in Example 50 step 5 and making variations as required to replace 4-(adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid with 4-(adamantan-1-ylmethoxy)-5-chloro-2-fluorobenzoic acid and methanesulfonamide with 1-methyl-1H-imidazole-4-sulfonamide, the title compound was obtained as a colorless solid (0.16 g, 33%): 1H NMR (300 MHz, DMSO-d6) δ 8.03-8.01 (m, 1H), 7.85-7.80 (m, 1H), 7.66-7.60 (m, 1H), 7.21-7.14 (m, 1H), 3.73 (s, 3H), 3.70 (s, 2H), 1.98 (s, 3H), 1.78-1.57 (m, 12H); MS (ES+) m/z 482.2 (M+1), 484.2 (M+1).

Sources & evidence

ORD record
ord-20315add3922492ba107b7abb33eed38
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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