2-(Tricyclo(3.3.1.1'3,7)dec-1-yl)ethanol → 4-(2-(adamantan-1-yl)ethoxy)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamide

HRID 1427803Notes

Reaction equation

HRID 1427803 reaction equation
C1(CCO)CC1.[C:7]12([CH2:17][CH2:18][OH:19])[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH2:8]1)[CH2:14]2.FC1C=C(F)C(F)=CC=1C(NS(C)(=O)=O)=O.[Cl:36][C:37]1[C:38](F)=[CH:39][C:40]([F:50])=[C:41]([CH:49]=1)[C:42]([NH:44][S:45]([CH3:48])(=[O:47])=[O:46])=[O:43]>>[C:7]12([CH2:17][CH2:18][O:19][C:38]3[C:37]([Cl:36])=[CH:49][C:41]([C:42]([NH:44][S:45]([CH3:48])(=[O:47])=[O:46])=[O:43])=[C:40]([F:50])[CH:39]=3)[CH2:14][CH:13]3[CH2:12][CH:11]([CH2:10][CH:9]([CH2:15]3)[CH2:8]1)[CH2:16]2

Participants

5

Reactant 4

HCID 1108102-(Tricyclo(3.3.1.1'3,7)dec-1-yl)ethanolHCID 1376422-Cyclopropylethan-1-olHCID 580424175-chloro-2,4-difluoro-N-(methylsulfonyl)benzamideHCID 580424352,4,5-trifluoro-N-(methylsulfonyl)benzamide

Product 1

HCID 725456714-(2-(adamantan-1-yl)ethoxy)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamide

Procedure

Following the procedure as described in Example 1 and making variations as required to replace 2-cyclopropylethanol with 2-(adamantan-1-yl)ethanol and 2,4,5-trifluoro-N-(methylsulfonyl)benzamide with 5-chloro-2,4-difluoro-N-(methylsulfonyl)-benzamide, the title compound was obtained as a colorless solid (0.04 g, 5%): 1H NMR (300 MHz, DMSO-d6) δ 12.06 (s, 1H), 7.73 (d, J=7.5 Hz, 1H), 7.26 (d, J=12.6 Hz, 1H), 4.15 (t, J=6.9 Hz, 2H), 3.31 (s, 3H), 1.89 (br s, 3H), 1.66-1.51 (m, 14H); 13C NMR (75 MHz, DMSO-d6) δ 162.3 (d, JC-F=2 Hz), 159.9 (d, JC-F=254 Hz), 158.1 (d, JC-F=12 Hz), 130.7 (d, JC-F=4 Hz), 116.5 (d, JC-F=3 Hz), 113.6 (d, JC-F=14 Hz), 102.5 (d, JC-F=28 Hz), 66.1, 42.1, 41.8, 41.2, 36.4, 31.3, 27.9; MS (ES−) m/z 428.1, 430.1 (M−1).

Sources & evidence

ORD record
ord-b5c862e8ba5442b79c1a75509a4d9513
Source dataset
uspto-grants-2015_01
Patent number
US08933236B2

Reaction notes

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