5-chloro-2,4-difluoro-N-(methylsulfonyl)benzamide → 4-(adamantan-1-ylmethoxy)-5-chloro-N-(N,N-dimethylsulfamoyl)-2-fluorobenzamide

HRID 1427808Notes

Reaction equation

HRID 1427808 reaction equation
Cl[C:2]1[C:3](F)=[CH:4][C:5](F)=[C:6]([CH:14]=1)[C:7](NS(C)(=O)=O)=[O:8].[Cl:17][C:18]1[C:19](F)=[CH:20][C:21]([F:33])=[C:22]([CH:32]=1)[C:23]([NH:25][S:26](=[O:31])(=[O:30])[N:27]([CH3:29])[CH3:28])=[O:24]>>[C:6]12([CH2:7][O:8][C:19]3[C:18]([Cl:17])=[CH:32][C:22]([C:23]([NH:25][S:26](=[O:31])(=[O:30])[N:27]([CH3:29])[CH3:28])=[O:24])=[C:21]([F:33])[CH:20]=3)[CH2:5][CH:4]3[CH2:5][CH:6]([CH2:14][CH:2]([CH2:3]3)[CH2:14]1)[CH2:7]2

Participants

3

Reactant 2

HCID 580424175-chloro-2,4-difluoro-N-(methylsulfonyl)benzamideHCID 867028365-chloro-N-(N,N-dimethylsulfamoyl)-2,4-difluorobenzamide

Product 1

HCID 867028354-(adamantan-1-ylmethoxy)-5-chloro-N-(N,N-dimethylsulfamoyl)-2-fluorobenzamide

Procedure

Following the procedure as described in Example 8 and making variations as required to replace 5-chloro-2,4-difluoro-N-(methylsulfonyl)benzamide with 5-chloro-N—(N,N-dimethylsulfamoyl)-2,4-difluorobenzamide (as prepared in Example 31), the title compound was obtained as a colorless solid (0.25 g, 38%): 1H NMR (300 MHz, DMSO-d6) δ 11.77 (s, 1H), 7.72 (d, J=7.45 Hz 1H), 7.22 (d, J=12.3 Hz, 1H), 3.72 (s, 2H), 2.87 (s, 6H), 1.99 (br, 3H), 1.75-1.64 (m, 12H); MS (ES−) m/z 443.1, 445.1 (M−1).

Sources & evidence

ORD record
ord-088a31c083a44d82bc3a8613cea0f3a9
Source dataset
uspto-grants-2015_01
Patent number
US08933236B2

Reaction notes

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