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Dibutylamine → N,N-Dibutyl-2-[3-(2,2-dimethylpropanoyl)-6-methoxy-1H-indazol-1-yl]acetamide

HRID 490793
Notes
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Reaction equation

HRID 490793 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]([OH:19])=O)[N:6]=1)=[O:4].C1C=CC2N(O)N=NC=2C=1.[CH2:32]([NH:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:33][CH2:34][CH3:35].CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)CCl>[CH2:32]([N:36]([CH2:37][CH2:38][CH2:39][CH3:40])[C:17](=[O:19])[CH2:16][N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)[C:5]([C:3](=[O:4])[C:2]([CH3:20])([CH3:1])[CH3:21])=[N:6]1)[CH2:33][CH2:34][CH3:35]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8148DibutylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57675531[3-(2,2-Dimethylpropanoyl)-6-methoxy-1H-indazol-1-yl]acetic acid

Product 1

HCID 10453694N,N-Dibutyl-2-[3-(2,2-dimethylpropanoyl)-6-methoxy-1H-indazol-1-yl]acetamide

Reagents, catalysts & solvents 2

HCID 11
1,2-Dichloroethane
Solvent
HCID 6228DimethylformamideSolvent

Procedure

To a solution of 28.3 mg [3-(2,2-dimethylpropanoyl)-6-methoxy-1H-indazol-1-yl]acetic acid from the Step E above in 1 mL DMF was added 23.0 mg HOBt, 19.4 mg dibutylamine, 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: 4.33 min. (m/Z=402.3, 424.3).

Workup

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

Sources & evidence

ORD record
ord-e31cbd1cb0d54050af4ef54d3d3540f3
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07528163B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes