Methanesulfonamide → 4-(adamantan-1-ylmethoxy)-3,5-dichloro-N-(methylsulfonyl)benzamide

HRID 1849712Notes

Reaction equation

HRID 1849712 reaction equation
C12(COC3C(C4CC4)=CC(C(O)=O)=CN=3)CC3CC(CC(C3)C1)C2.[C:25]12([CH2:35][O:36][C:37]3[C:45]([Cl:46])=[CH:44][C:40]([C:41](O)=[O:42])=[CH:39][C:38]=3[Cl:47])[CH2:34][CH:29]3[CH2:30][CH:31]([CH2:33][CH:27]([CH2:28]3)[CH2:26]1)[CH2:32]2.COC[CH2:51][S:52]([NH2:55])(=[O:54])=[O:53].CS(N)(=O)=O>>[C:25]12([CH2:35][O:36][C:37]3[C:45]([Cl:46])=[CH:44][C:40]([C:41]([NH:55][S:52]([CH3:51])(=[O:54])=[O:53])=[O:42])=[CH:39][C:38]=3[Cl:47])[CH2:34][CH:29]3[CH2:30][CH:31]([CH2:33][CH:27]([CH2:28]3)[CH2:26]1)[CH2:32]2

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 189515062-Methoxyethane-1-sulfonamideHCID 867029246-(Adamantan-1-ylmethoxy)-5-cyclopropylnicotinic acidHCID 867035864-(Adamantan-1-ylmethoxy)-3,5-dichlorobenzoic acid

Product 1

HCID 867035874-(adamantan-1-ylmethoxy)-3,5-dichloro-N-(methylsulfonyl)benzamideYield 74%

Procedure

Following the procedure as described in Example 271 and making variations as required to replace 6-(adamantan-1-ylmethoxy)-5-cyclopropylnicotinic acid with 4-(adamantan-1-ylmethoxy)-3,5-dichlorobenzoic acid and to replace 2-methoxyethanesulfonamide with methyl sulfonamide. Purification by silica gel column chromatography (2:1 hexanes:ethyl acetate (+0.2% acetic acid v/v)) gave the title compound as a colorless solid (0.72 g, 74%): 1H NMR (300 MHz, DMSO-d6) δ 12.20 (br s, 1H), 8.01 (s, 2H), 3.55 (s, 2H), 3.33 (s, 3H), 1.99-1.91 (m, 3H), 1.72-1.57 (m, 12H); MS (ES−) m/z 430.1, 432.1 (M−1).

Workup

  1. customPurification by silica gel column chromatography (2:1 hexanes

Sources & evidence

ORD record
ord-ba4c57f7c6214635a6546696ad4a4939
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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