4-Aminoadamantan-1-ol → 3-[2-(1-Cyclopropanesulfonyl-piperidin-4-yl)-ethoxy]-N-(5-hydroxy-adamantan-2-yl)-benzamide

HRID 1401148Notes

Reaction equation

HRID 1401148 reaction equation
[CH:1]1([S:4]([N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][CH2:14][O:15][C:16]3[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=3)[C:19]([OH:21])=O)[CH2:9][CH2:8]2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[NH2:25][CH:26]1[CH:33]2[CH2:34][C:29]3([OH:36])[CH2:30][CH:31]([CH2:35][CH:27]1[CH2:28]3)[CH2:32]2>>[CH:1]1([S:4]([N:7]2[CH2:8][CH2:9][CH:10]([CH2:13][CH2:14][O:15][C:16]3[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=3)[C:19]([NH:25][CH:26]3[CH:27]4[CH2:35][CH:31]5[CH2:30][C:29]([OH:36])([CH2:34][CH:33]3[CH2:32]5)[CH2:28]4)=[O:21])[CH2:11][CH2:12]2)(=[O:5])=[O:6])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 28574474-Aminoadamantan-1-olHCID 669301013-[2-(1-Cyclopropanesulfonyl-piperidin-4-yl)-ethoxy]-benzoic acid

Product 1

HCID 252423283-[2-(1-Cyclopropanesulfonyl-piperidin-4-yl)-ethoxy]-N-(5-hydroxy-adamantan-2-yl)-benzamide

Procedure

Prepared from 3-[2-(1-cyclopropanesulfonyl-piperidin-4-yl)-ethoxy]-benzoic acid and 4-amino-1-hydroxyadamantane. 1H NMR (400 MHz, CDCl3): δ 7.32-7.38 (m, 2H), 7.24-7.26 (m, 1H), 7.03 (dd, 1H), 6.32 (d, 1H), 4.19-4.24 (m, 1H), 4.07 (t, 2H), 3.78-3.85 (m, 2H), 2.81 (td, 2H), 2.61 (br. s., 2H), 2.22-2.29 (m, 3H), 2.18-2.22 (m, 1H), 1.95 (d, 2H), 1.73-1.89 (m, 11H), 1.65-1.73 (m, 1H), 1.59 (d, 2H), 1.41 (dd, 1H), 1.35 (dd, 1H), 1.14-1.20 (m, 2H), 0.94-1.00 (m, 2H).

Sources & evidence

ORD record
ord-19b258bc16584228b92ffd2bcfd8af0d
Source dataset
uspto-grants-2014_12
Patent number
US08907096B2

Reaction notes

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