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

HRID 490793Notes

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]

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 111,2-DichloroethaneSolventHCID 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
Patent number
US07528163B2

Reaction notes

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