4-(adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluoro-N-((2-methoxyethyl)sulfonyl)benzamide → 4-(adamantan-1-ylmethoxy)-5-chloro-2-fluoro-N-((2-hydroxyethyl)-sulfonyl)benzamide

HRID 1427879Notes

Reaction equation

HRID 1427879 reaction equation
C12(COC3C(C4CC4)=CC(C(NS(CCOC)(=O)=O)=O)=C(F)C=3)CC3CC(CC(C3)C1)C2.[C:33]12([CH2:43][O:44][C:45]3[C:60]([Cl:61])=[CH:59][C:48]([C:49]([NH:51][S:52]([CH2:55][CH2:56][O:57]C)(=[O:54])=[O:53])=[O:50])=[C:47]([F:62])[CH:46]=3)[CH2:42][CH:37]3[CH2:38][CH:39]([CH2:41][CH:35]([CH2:36]3)[CH2:34]1)[CH2:40]2>>[C:33]12([CH2:43][O:44][C:45]3[C:60]([Cl:61])=[CH:59][C:48]([C:49]([NH:51][S:52]([CH2:55][CH2:56][OH:57])(=[O:54])=[O:53])=[O:50])=[C:47]([F:62])[CH:46]=3)[CH2:34][CH:35]3[CH2:41][CH:39]([CH2:38][CH:37]([CH2:36]3)[CH2:42]1)[CH2:40]2

Participants

3

Reactant 2

HCID 867029024-(adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluoro-N-((2-methoxyethyl)sulfonyl)benzamideHCID 867029034-(adamantan-1-ylmethoxy)-5-chloro-2-fluoro-N-((2-methoxyethyl)sulfonyl)benzamide

Product 1

HCID 867029044-(adamantan-1-ylmethoxy)-5-chloro-2-fluoro-N-((2-hydroxyethyl)-sulfonyl)benzamide

Procedure

Following the procedure as described in Example 121 and making variation as required to replace 4-(adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluoro-N-((2-methoxyethyl)sulfonyl)benzamide with 4-(adamantan-1-ylmethoxy)-5-chloro-2-fluoro-N-((2-methoxyethyl)sulfonyl)benzamide, the title compound was obtained as a colorless solid (0.04 g, 15%): 1H NMR (300 MHz, CDCl3) δ 8.74-8.61 (m, 1H), 8.11-8.03 (m, 1H), 6.75-6.64 (m, 1H), 4.23-4.08 (m, 2H), 3.86-3.76 (m, 2H), 3.59 (s, 2H), 2.50-2.40 (m, 1H), 2.12-1.96 (m, 3H), 1.86-1.62 (m, 12H); MS (ES−) m/z 444.3 (M−1), 446.3 (M−1);

Sources & evidence

ORD record
ord-25f7baab404449ada8f047dfe3e9f575
Source dataset
uspto-grants-2015_01
Patent number
US08933236B2

Reaction notes

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