2-Adamantanol → 4-(adamantan-2-yloxy)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamide

HRID 1427801Notes

Reaction equation

HRID 1427801 reaction equation
C1(CCO)CC1.[CH:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH:8]1[OH:17])[CH2:14]2.FC1C=C(F)C(F)=CC=1C(NS(C)(=O)=O)=O.[Cl:34][C:35]1[C:36](F)=[CH:37][C:38]([F:48])=[C:39]([CH:47]=1)[C:40]([NH:42][S:43]([CH3:46])(=[O:45])=[O:44])=[O:41]>>[CH:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH:8]1[O:17][C:36]1[C:35]([Cl:34])=[CH:47][C:39]([C:40]([NH:42][S:43]([CH3:46])(=[O:45])=[O:44])=[O:41])=[C:38]([F:48])[CH:37]=1)[CH2:14]2

Participants

5

Reactant 4

HCID 641492-AdamantanolHCID 1376422-Cyclopropylethan-1-olHCID 580424175-chloro-2,4-difluoro-N-(methylsulfonyl)benzamideHCID 580424352,4,5-trifluoro-N-(methylsulfonyl)benzamide

Product 1

HCID 725456704-(adamantan-2-yloxy)-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-2-ol 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 (0.055 g, 4%): 1H NMR (300 MHz, DMSO-d6) δ 12.07 (s, 1H), 7.78 (d, J=7.5 Hz, 1H), 7.33 (d, J=12.6 Hz, 1H), 4.82 (br s, 1H), 3.34 (s, 3H), 2.08-2.03 (m, 4H), 1.84 (br s, 6H), 1.71 (br s, 2H), 1.55-1.51 (m, 2H); MS (ES−) m/z 400.1, 402.1 (M−1).

Sources & evidence

ORD record
ord-5230aac05de045c88bc56ca747966227
Source dataset
uspto-grants-2015_01
Patent number
US08933236B2

Reaction notes

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