1,2-Dichloroethane → N-(3,3-Dimethylbutyl)-3-(2,2-dimethyl-1-oxopropyl)-N-ethyl-6-methoxy-1H-indazole-1-acetamide

HRID 490806Notes

Reaction equation

HRID 490806 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=C[C:25]2N(O)N=N[C:26]=2[CH:27]=1.[CH2:32](Cl)CCl.CC[N:38]([CH:42]([CH3:44])C)[CH:39]([CH3:41])C>CN(C=O)C>[CH3:32][C:26]([CH3:25])([CH3:27])[CH2:44][CH2:42][N:38]([CH2:39][CH3:41])[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]([CH3:21])([CH3:20])[CH3:1])=[N:6]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57675531[3-(2,2-Dimethylpropanoyl)-6-methoxy-1H-indazol-1-yl]acetic acid

Product 1

HCID 10341009N-(3,3-Dimethylbutyl)-3-(2,2-dimethyl-1-oxopropyl)-N-ethyl-6-methoxy-1H-indazole-1-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 29.0 mg [3-(2,2-dimethylpropanoyl)-6-methoxy-1H-indazol-1-yl]acetic acid in 1 mL DMF was added 23.0 mg HOBt, 32.3 mg N-Ethyl-3,3-dimethylbutan-1-lamine hydrochloride from the Step A above, 38.3 mg EDC, and 45.2 mg DIEA in that order. The mixture was stirred at room temperature for four hours and heated at 45° C. over night and purified by RP-HPLC using 70-100% MeCN gradient. The pure product fractions were pooled and lyophilized to give the title compound. LC-MS: 4.29 min. (m/Z=402.4, 424.3).

Workup

  1. temperatureheated at 45° C. over night
  2. custompurified by RP-HPLC using 70-100% MeCN gradient

Sources & evidence

ORD record
ord-5e23dd7656594e2dbf304fa91e168f28
Source dataset
uspto-grants-2009_05
Patent number
US07528163B2

Reaction notes

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