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

HRID 1427846Notes

Reaction equation

HRID 1427846 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.[CH:47]([C@H:50]1[CH2:55][CH2:54][C@H:53]([OH:56])[CH2:52][CH2:51]1)([CH3:49])[CH3:48]>>[Cl:17][C:18]1[C:19]([O:56][C@H:53]2[CH2:54][CH2:55][C@H:50]([CH:47]([CH3:49])[CH3:48])[CH2:51][CH2:52]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 580424175-chloro-2,4-difluoro-N-(methylsulfonyl)benzamideHCID 867028365-chloro-N-(N,N-dimethylsulfamoyl)-2,4-difluorobenzamideHCID 178448130HCID 178448130, compound

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 trans-4-isopropylcyclohexanol, the title compound was obtained as a colorless solid (0.10 g, 24%): 1H NMR (300 MHz, DMSO-d6) δ 11.75 (s, 1H), 7.71 (d, J=7.5 Hz, 1H), 7.34 (d, J=12.5 Hz, 1H), 4.53-4.43 (m, 1H), 2.87 (s, 6H), 2.11-2.07 (m, 2H), 1.75-1.71 (m, 2H), 1.50-1.20 (m, 3H), 1.24-1.07 (m, 3H), 0.86 (d, J=6.8 Hz, 6H); MS (ES−) m/z 419.1, 421.1 (M−1).

Sources & evidence

ORD record
ord-566c49d23c7345f7b3cbe01ff557f460
Source dataset
uspto-grants-2015_01
Patent number
US08933236B2

Reaction notes

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