Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol → 4-(2-(adamantan-1-yl)ethoxy)-5-chloro-N-(N,N-dimethylsulfamoyl)-2-fluorobenzamide

HRID 1849541Notes

Reaction equation

HRID 1849541 reaction equation
ClC1C(F)=CC(F)=[C:6](C=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:35]12(CO)[CH2:44][CH:39]3[CH2:40][CH:41]([CH2:43][CH:37]([CH2:38]3)[CH2:36]1)[CH2:42]2.C12(C(O)C)CC3CC(CC(C3)C1)C2>>[C:35]12([CH2:6][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)[CH2:36][CH:37]3[CH2:43][CH:41]([CH2:40][CH:39]([CH2:38]3)[CH2:44]1)[CH2:42]2

Participants

5

Reactant 4

HCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 27697131-(1-Adamantyl)ethanolHCID 580424175-chloro-2,4-difluoro-N-(methylsulfonyl)benzamideHCID 867028365-chloro-N-(N,N-dimethylsulfamoyl)-2,4-difluorobenzamide

Product 1

HCID 867028854-(2-(adamantan-1-yl)ethoxy)-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 and adamantan-1-ylmethanol with adamantan-1-ylethanol, the title compound was obtained as a colorless solid (0.15 g, 33%): 1H NMR (300 MHz, DMSO-d6) δ 11.75 (s, 1H), 7.72 (d, J=7.5 Hz, 1H), 7.28 (d, J=12.5 Hz, 1H), 4.18 (t, J=7.0 Hz, 2H), 2.87 (s, 6H), 1.93-1.88 (br s, 3H), 1.70-1.54 (m, 14H); MS (ES−) m/z 457.2, 459.2 (M−1).

Sources & evidence

ORD record
ord-96be0ffcc221434baf7e22d9b49dc014
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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