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

HRID 1427800Notes

Reaction equation

HRID 1427800 reaction equation
C1(CCO)CC1.[C:7]12([CH2:17][OH:18])[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:35][C:36]1[C:37](F)=[CH:38][C:39]([F:49])=[C:40]([CH:48]=1)[C:41]([NH:43][S:44]([CH3:47])(=[O:46])=[O:45])=[O:42]>>[C:7]12([CH2:17][O:18][C:37]3[C:36]([Cl:35])=[CH:48][C:40]([C:41]([NH:43][S:44]([CH3:47])(=[O:46])=[O:45])=[O:42])=[C:39]([F:49])[CH:38]=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 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 1376422-Cyclopropylethan-1-olHCID 580424175-chloro-2,4-difluoro-N-(methylsulfonyl)benzamideHCID 580424352,4,5-trifluoro-N-(methylsulfonyl)benzamide

Product 1

HCID 725456694-(adamantan-1-ylmethoxy)-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 adamantan-1-ylmethanol and 2,4,5-trifluoro-N-(methylsulfonyl)benzamide with 5-chloro-2,4-difluoro-N-(methylsulfonyl)benzamide (WO 2012007883 A1), the title compound was obtained as a colorless solid (0.20 g, 8%): 1H NMR (300 MHz, DMSO-d6) δ 12.10 (s, 1H), 7.77 (d, J=7.5 Hz 1H), 7.23 (d, J=12.5 Hz, 1H), 3.72 (s, 2H), 3.35 (s, 3H), 1.99 (br s, 3H), 1.75-1.64 (m, 12H); 13C NMR (75 MHz, DMSO-d6) δ 162.3 (d, J=2.0 Hz), 159.8 (d, JC-F=255 Hz), 158.3 (d, JC-F=11 Hz), 130.6 (d, JC-F=4 Hz), 116.8 (d, JC-F=3 Hz), 113.6 (d, JC-F=14 Hz), 102.7 (d, JC-F=28 Hz), 79.1, 41.2, 38.5, 36.4, 33.4, 27.3; MS (ES+) m/z 415.6, 417.6 (M+1).

Sources & evidence

ORD record
ord-501fa7a29dde4d62a0cb4a11ba849980
Source dataset
uspto-grants-2015_01
Patent number
US08933236B2

Reaction notes

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