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

HRID 1849634Notes

Reaction equation

HRID 1849634 reaction equation
[C:1]12([CH2:11][O:12][C:13]3[C:28]([CH:29]4[CH2:31][CH2:30]4)=[CH:27][C:16]([C:17]([NH:19][S:20]([CH2:23][CH2:24][O:25]C)(=[O:22])=[O:21])=[O:18])=[C:15]([F:32])[CH:14]=3)CC3C[CH:7]([CH2:9][CH:3](C3)[CH2:2]1)[CH2:8]2.C1(COC2C(C3CC3)=CC(C(NS(CCOC)(=O)=O)=O)=C(F)C=2)CCCCC1>>[CH:1]1([CH2:11][O:12][C:13]2[C:28]([CH:29]3[CH2:30][CH2:31]3)=[CH:27][C:16]([C:17]([NH:19][S:20]([CH2:23][CH2:24][OH:25])(=[O:21])=[O:22])=[O:18])=[C:15]([F:32])[CH:14]=2)[CH2:2][CH2:3][CH2:9][CH2:7][CH2:8]1

Participants

3

Reactant 2

HCID 867029024-(adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluoro-N-((2-methoxyethyl)sulfonyl)benzamideHCID 867034914-(cyclohexylmethoxy)-5-cyclopropyl-2-fluoro-N-((2-methoxyethyl)-sulfonyl)benzamide

Product 1

HCID 867034934-(cyclohexylmethoxy)-5-cyclopropyl-2-fluoro-N-((2-hydroxyethyl)-sulfonyl)benzamide

Procedure

Following the procedure as described in Example 121 and making variations as required to replace 4-(adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluoro-N-((2-methoxyethyl)-sulfonyl)benzamide with 4-(cyclohexylmethoxy)-5-cyclopropyl-2-fluoro-N-((2-methoxyethyl)-sulfonyl)benzamide, the title compound was obtained as colorless solid (0.03 g, 14%): 1H NMR (300 MHz, CDCl3) δ8.77-8.65 (m, 1H), 7.60-7.49 (m, 1H), 6.63-6.51 (m, 1H), 4.19-4.09 (m, 2H), 3.86-3.74 (m, 4H), 2.59-2.49 (m, 1H), 2.10-1.98 (m, 1H), 1.94-1.68 (m, 6H), 1.39-1.04 (m, 5H), 0.99-0.90 (m, 2H), 0.70-0.61 (m, 2H); MS (ES−) m/z 398.3 (M−1).

Sources & evidence

ORD record
ord-643e39eaea3d4d28975557208e792930
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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