Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol → HCID 72545917, compound

HRID 1849544Notes

Reaction equation

HRID 1849544 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.[Cl:47][C:48]12[CH2:57][CH:52]3[CH2:53][CH:54]([CH2:56][C:50]([CH2:58][OH:59])([CH2:51]3)[CH2:49]1)[CH2:55]2>>[Cl:17][C:18]1[C:19]([O:59][CH2:58][C:50]23[CH2:51][CH:52]4[CH2:53][CH:54]([CH2:55][C:48]([Cl:47])([CH2:57]4)[CH2:49]2)[CH2:56]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 3091320HCID 3091320, compoundHCID 580424175-chloro-2,4-difluoro-N-(methylsulfonyl)benzamideHCID 867028365-chloro-N-(N,N-dimethylsulfamoyl)-2,4-difluorobenzamide

Product 1

HCID 72545917HCID 72545917, 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 3-chloroadamantan-1-yl methanol, the title compound was obtained as a colorless solid (0.15 g, 31%): 1H NMR (300 MHz, DMSO-d6) δ 11.77 (s, 1H), 7.74 (d, J=7.4 Hz, 1H), 7.23 (d, J=12.3 Hz, 1H), 3.82 (s, 2H), 2.87 (s, 6H), 2.22 (br s, 2H), 2.14-2.02 (m, 6H), 1.70-1.55 (s, 6H); MS (ES−) m/z 477.1, 479.1 (M−1).

Sources & evidence

ORD record
ord-8e1312c1aa8f48ef8cddc5ec1eafd4c5
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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