2-Adamantanol → 4-(adamantan-2-yloxy)-5-chloro-N-(N,N-dimethylsulfamoyl)-2-fluorobenzamide

HRID 1427809Notes

Reaction equation

HRID 1427809 reaction equation
C12(CO)CC3CC(CC(C3)C1)C2.[CH:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH:14]1[OH:23])[CH2:20]2.ClC1C(F)=CC(F)=C(C=1)C(NS(C)(=O)=O)=O.[Cl:40][C:41]1[C:42](F)=[CH:43][C:44]([F:56])=[C:45]([CH:55]=1)[C:46]([NH:48][S:49](=[O:54])(=[O:53])[N:50]([CH3:52])[CH3:51])=[O:47]>>[CH:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH:14]1[O:23][C:42]1[C:41]([Cl:40])=[CH:55][C:45]([C:46]([NH:48][S:49](=[O:54])(=[O:53])[N:50]([CH3:52])[CH3:51])=[O:47])=[C:44]([F:56])[CH:43]=1)[CH2:20]2

Participants

5

Reactant 4

HCID 641492-AdamantanolHCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 580424175-chloro-2,4-difluoro-N-(methylsulfonyl)benzamideHCID 867028365-chloro-N-(N,N-dimethylsulfamoyl)-2,4-difluorobenzamide

Product 1

HCID 867028374-(adamantan-2-yloxy)-5-chloro-N-(N,N-dimethylsulfamoyl)-2-fluorobenzamide

Procedure

Following the procedure as described in Example 8 and making variations as required to replace adamantan-1-ylmethanol with adamantan-2-ol and 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 (0.21 g, 38%): 1H NMR (300 MHz, DMSO-d6) δ 11.73 (s, 1H), 7.74 (d, J=7.5 Hz, 1H), 7.33 (d, J=12.5 Hz, 1H), 4.81 (s, 1H), 2.87 (s, 6H), 2.08-2.03 (m, 4H), 1.84-1.71 (m, 8H), 1.54-1.50 (m, 2H); MS (ES−) m/z 429.2, 431.2 (M−1).

Sources & evidence

ORD record
ord-3d804fba4f064642b27f4c1af4cb5338
Source dataset
uspto-grants-2015_01
Patent number
US08933236B2

Reaction notes

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