5-chloro-2,4-difluoro-N-(methylsulfonyl)benzamide → 4-(adamantan-1-ylmethoxy)-3-chloro-N-(methylsulfonyl)benzamide

HRID 1427806Notes

Reaction equation

HRID 1427806 reaction equation
[Cl:1][C:2]1[C:3](F)=[CH:4][C:5](F)=[C:6]([CH:14]=1)[C:7]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[O:8].Cl[C:18]1[CH:19]=[C:20]([CH:28]=[CH:29][C:30]=1F)[C:21](NS(C)(=O)=O)=[O:22]>>[C:20]12([CH2:21][O:22][C:3]3[CH:4]=[CH:5][C:6]([C:7]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[O:8])=[CH:14][C:2]=3[Cl:1])[CH2:28][CH:29]3[CH2:5][CH:6]([CH2:14][CH:18]([CH2:30]3)[CH2:19]1)[CH2:7]2

Participants

3

Reactant 2

HCID 580424175-chloro-2,4-difluoro-N-(methylsulfonyl)benzamideHCID 867028333-chloro-4-fluoro-N-(methylsulfonyl)benzamide

Product 1

HCID 867028324-(adamantan-1-ylmethoxy)-3-chloro-N-(methylsulfonyl)benzamide

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 3-chloro-4-fluoro-N-(methylsulfonyl)benzamide, the title compound was obtained as a colorless solid (0.34 g, 52%): 1H NMR (300 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.04-7.94 (m, 2H), 7.25 (d, J=8.5 Hz, 1H), 3.72 (s, 2H), 3.36 (s, 3H), 1.99 (br, 3H), 1.71-1.66 (m, 12H); MS (ES−) m/z 396.1, 398.1 (M−1).

Sources & evidence

ORD record
ord-f33b64177a624555954d02c344eee169
Source dataset
uspto-grants-2015_01
Patent number
US08933236B2

Reaction notes

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