Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol → HCID 72545920, compound

HRID 1849576Notes

Reaction equation

HRID 1849576 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]12[CH2:56][CH:51]3[CH2:52][CH:53]([CH2:55][CH:49]([CH2:50]3)[CH:48]1[CH2:57][OH:58])[CH2:54]2>>[CH:47]12[CH2:56][CH:51]3[CH2:52][CH:53]([CH2:55][CH:49]([CH2:50]3)[CH:48]1[CH2:57][O:58][C:19]1[C:18]([Cl:17])=[CH:32][C:22]([C:23]([NH:25][S:26](=[O:31])(=[O:30])[N:27]([CH3:29])[CH3:28])=[O:24])=[C:21]([F:33])[CH:20]=1)[CH2:54]2

Participants

5

Reactant 4

HCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 132917312-AdamantanemethanolHCID 580424175-chloro-2,4-difluoro-N-(methylsulfonyl)benzamideHCID 867028365-chloro-N-(N,N-dimethylsulfamoyl)-2,4-difluorobenzamide

Product 1

HCID 72545920HCID 72545920, 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 adamantan-2-ylmethanol (J. Am. Chem. Soc. 2012, 134(2), 675), the title compound was obtained as a colorless solid (0.14 g, 27%): 1H NMR (300 MHz, CDCl3) δ 8.75-8.57 (m, 1H), 8.13-8.03 (m, 1H), 6.82-6.67 (m, 1H), 4.23-4.03 (m, 2H), 3.03 (s, 6H), 2.37-2.27 (m, 1H), 2.04-1.73 (m, 11H), 1.69-1.54 (m, 3H); MS (ES−) m/z 443.2 (M−1), 445.2 (M−1);

Sources & evidence

ORD record
ord-676b33627c05416cb13559c2c39d48c9
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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