Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol → HCID 86702887, compound

HRID 1849543Notes

Reaction equation

HRID 1849543 reaction equation
ClC1C(F)=CC(F)=C(C=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].C12(CO)CC3CC(CC(C3)C1)C2.[CH2:47]([C:52]12[CH2:59][CH2:58][C:55]([CH2:60][OH:61])([CH2:56][CH2:57]1)[CH2:54][CH2:53]2)[CH2:48][CH2:49][CH2:50][CH3:51]>>[Cl:17][C:18]1[C:19]([O:61][CH2:60][C:55]23[CH2:56][CH2:57][C:52]([CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])([CH2:59][CH2:58]2)[CH2:53][CH2:54]3)=[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 20257153(4-Pentylbicyclo[2.2.2]octan-1-yl)methanolHCID 580424175-chloro-2,4-difluoro-N-(methylsulfonyl)benzamideHCID 867028365-chloro-N-(N,N-dimethylsulfamoyl)-2,4-difluorobenzamide

Product 1

HCID 86702887HCID 86702887, 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 (4-pentylbicyclo[2.2.2]octan-1-yl)methanol, the title compound was obtained as a colorless solid (0.25 g, 51%): 1H NMR (300 MHz, DMSO-d6) δ 11.75 (s, 1H), 7.71 (d, J=7.5 Hz, 1H), 7.19 (d, J=12.4 Hz, 1H), 3.76 (s, 2H), 2.87 (s, 6H), 1.53-1.48 (m, 6H), 1.38-1.06 (m, 14H), 0.85 (t, J=7.0 Hz, 3H); MS (ES−) m/z 487.2, 489.2 (M−1).

Sources & evidence

ORD record
ord-509aee6b71944337a024769e4bfe40c7
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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