Methanesulfonamide → 4-(adamantan-2-yl)-3-chloro-N-(N-methylsulfamoyl)benzamide

HRID 1849790Notes

Reaction equation

HRID 1849790 reaction equation
CS(N)(=O)=O.[CH3:6][NH:7][S:8]([NH2:11])(=[O:10])=[O:9].C(C1(COC2C(C3CC3)=CC(C(O)=O)=C(F)C=2)C2CC3CC(CC1C3)C2)#N.[CH:39]12[CH2:48][CH:43]3[CH2:44][CH:45]([CH2:47][CH:41]([CH2:42]3)[CH:40]1[C:49]1[CH:57]=[CH:56][C:52]([C:53](O)=[O:54])=[CH:51][C:50]=1[Cl:58])[CH2:46]2>>[CH:39]12[CH2:48][CH:43]3[CH2:44][CH:45]([CH2:47][CH:41]([CH2:42]3)[CH:40]1[C:49]1[CH:57]=[CH:56][C:52]([C:53]([NH:11][S:8](=[O:10])(=[O:9])[NH:7][CH3:6])=[O:54])=[CH:51][C:50]=1[Cl:58])[CH2:46]2

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 13168287(Methylsulfamoyl)amineHCID 867036554-((2-Cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acidHCID 867036714-(Adamantan-2-yl)-3-chlorobenzoic acid

Product 1

HCID 867036724-(adamantan-2-yl)-3-chloro-N-(N-methylsulfamoyl)benzamide

Procedure

Following the procedure as described in Example 332 Step 7 and making non-critical variations to replace methanesulfonamide with methyl sulfamide and to replace 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid with 4-(adamantan-2-yl)-3-chlorobenzoic acid, the title compound was obtained following trituration with hexanes as a colorless solid (0.11 g, 66%): 1H NMR (300 MHz, DMSO-d6) δ 11.81 (s, 1H) 7.98-7.97 (m, 1H), 7.88-7.85 (m, 1H), 7.72 (d, J=8.2 Hz, 1H), 7.64-7.60 (m, 1H), 3.22 (s, 1H), 2.50 (d, J=4.4 Hz, 3H), 2.23 (s, 2H), 1.95-1.85 (m, 8H), 1.72 (s, 2H), 1.63-1.59 (m, 2H); MS (ES−) m/z 381.2, 383.2 (M−1).

Sources & evidence

ORD record
ord-f16e347802c9426f85b9b8512a3284cc
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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