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

HRID 1849712
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HRID 1849712 반응식
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
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참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-ba4c57f7c6214635a6546696ad4a4939
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08952169B2

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