Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol → HCID 178448127, compound

HRID 1849529Notes

Reaction equation

HRID 1849529 reaction equation
Cl[C:2]1C(F)=CC(F)=C([CH:14]=1)C(NS(C)(=O)=O)=O.[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)CC3CC(CC(C3)C1)C2.[CH:47]1([CH2:52][CH2:53][OH:54])[CH2:51][CH2:50][CH2:49]C1>>[Cl:17][C:18]1[C:19]([O:54][C@H:53]2[CH2:52][CH2:47][C@H:51]([CH:50]([CH3:49])[CH3:35])[CH2:14][CH2:2]2)=[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]

Participants

5

Reactant 4

HCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 69833CyclopentaneethanolHCID 580424175-chloro-2,4-difluoro-N-(methylsulfonyl)benzamideHCID 867028365-chloro-N-(N,N-dimethylsulfamoyl)-2,4-difluorobenzamide

Product 1

HCID 178448127HCID 178448127, compound

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 2-cyclopentylethanol, the title compound was obtained as a colorless solid (0.11 g, 29%): 1H NMR (300 MHz, DMSO-d6) δ 11.77 (s, 1H), 7.73 (d, J=7.5 Hz, 1H), 7.25 (d, J=12.4 Hz, 1H), 4.16 (t, J=6.5 Hz, 2H), 2.87 (s, 6H), 1.99-1.88 (m, 1H), 1.82-1.74 (m, 4H), 1.65-1.43 (m, 4H), 1.24-1.09 (m, 2H); MS (ES−) m/z 391.1, 393.1 (M−1).

Sources & evidence

ORD record
ord-bf69d57f44c84b00b64975086aecc898
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

Loading…