N-Ethyl cyclohexylamine → HCID 10093179, compound

HRID 490796Notes

Reaction equation

HRID 490796 reaction equation
[CH3:1][C:2]([CH3:21])([CH3:20])[C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[N:7]([CH2:16][C:17](O)=[O:18])[N:6]=1)=[O:4].[CH:22]1[CH:23]=[CH:24][C:25]2N(O)N=N[C:26]=2[CH:27]=1.[CH2:32]([NH:34][CH:35]1CCCCC1)[CH3:33].CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)CCl>[CH:26]1([CH2:35][N:34]([CH2:32][CH3:33])[C:17](=[O:18])[CH2:16][N:7]2[C:8]3[C:13](=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=3)[C:5]([C:3](=[O:4])[C:2]([CH3:20])([CH3:1])[CH3:21])=[N:6]2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:27]1

Participants

7

Reactant 4

HCID 21609N-Ethyl cyclohexylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57675531[3-(2,2-Dimethylpropanoyl)-6-methoxy-1H-indazol-1-yl]acetic acid

Product 1

HCID 10093179HCID 10093179, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 28.3 mg [3-(2,2-dimethylpropanoyl)-6-methoxy-1H-indazol-1-yl]acetic acid in 1 mL DMF was added 23.0 mg HOBt, 19.1 mg N-ethylcyclohexylamine, 38.3 mg EDC, and 45.2 mg DIEA in that order. The mixture was stirred at room temperature over night and purified by RP-HPLC using 65-100% MeCN gradient. The pure product fractions were pooled and lyophilized to give the title compound as white solid. LC-MS: 4.20 min. (m/Z=318.2, 400.3, 422.2).

Workup

  1. custompurified by RP-HPLC using 65-100% MeCN gradient

Sources & evidence

ORD record
ord-8316027761a74f45a838587068b3df48
Source dataset
uspto-grants-2009_05
Patent number
US07528163B2

Reaction notes

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