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

HRID 1427807Notes

Reaction equation

HRID 1427807 reaction equation
C12(CO)CC3CC(CC(C3)C1)C2.[C:13]12([CH2:23][CH2:24][OH:25])[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2.[Cl:26][C:27]1[C:28](F)=[CH:29][C:30](F)=[C:31]([CH:39]=1)[C:32]([NH:34][S:35]([CH3:38])(=[O:37])=[O:36])=[O:33].ClC1C=C(C=CC=1F)C(NS(C)(=O)=O)=O>>[C:13]12([CH2:23][CH2:24][O:25][C:28]3[CH:29]=[CH:30][C:31]([C:32]([NH:34][S:35]([CH3:38])(=[O:37])=[O:36])=[O:33])=[CH:39][C:27]=3[Cl:26])[CH2:20][CH:19]3[CH2:18][CH:17]([CH2:16][CH:15]([CH2:21]3)[CH2:14]1)[CH2:22]2

Participants

5

Reactant 4

HCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 1108102-(Tricyclo(3.3.1.1'3,7)dec-1-yl)ethanolHCID 580424175-chloro-2,4-difluoro-N-(methylsulfonyl)benzamideHCID 867028333-chloro-4-fluoro-N-(methylsulfonyl)benzamide

Product 1

HCID 867028344-(2-(adamantan-1-yl)ethoxy)-3-chloro-N-(methylsulfonyl)benzamide

Procedure

Following the procedure as described in Example 8 and making variations as required to replace adamantan-1-ylmethanol with 2-(adamantan-1-yl)ethanol and 5-chloro-2,4-difluoro-N-(methylsulfonyl)benzamide with 3-chloro-4-fluoro-N-(methylsulfonyl)benzamide, the title compound was obtained as a colorless solid (0.43 g, 71%): 1H NMR (300 MHz, DMSO-d6) 12.06 (s, 1H), 8.04 (d, J=2.2 Hz, 1H), 7.93 (dd, J=8.7 Hz, 2.2 Hz, 1H), 7.31 (d, J=8.7 Hz, 1H), 4.20 (t, J=6.9 Hz, 2H), 3.36 (s, 3H), 1.93 (br s, 3H), 1.70-1.55 (m, 14H); MS (ES+) m/z 411.8, 413.8 (M+1).

Sources & evidence

ORD record
ord-d5f78f0c8e284ae9b9f7aed7c3e99b71
Source dataset
uspto-grants-2015_01
Patent number
US08933236B2

Reaction notes

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