Diisopropylethylamine → N-(3,3-Dimethylbutyl)-N-ethyl-2-(3-isobutyryl-6-methoxy-1H-indazol-1-yl)acetamide

HRID 229460Notes

Reaction equation

HRID 229460 reaction equation
[C:1]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[N:8]([CH2:17][C:18]([OH:20])=O)[N:7]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].C1C=C2N=NN(O)C2=CC=1.O.Cl.[CH2:33]([NH:35][CH2:36][CH2:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH3:34].CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[CH3:39][C:38]([CH3:41])([CH3:40])[CH2:37][CH2:36][N:35]([CH2:33][CH3:34])[C:18](=[O:20])[CH2:17][N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)[C:6]([C:1](=[O:5])[CH:2]([CH3:3])[CH3:4])=[N:7]1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 57675517(3-Isobutyryl-6-methoxy-1H-indazol-1-yl)acetic acidHCID 71374414N-Ethyl-3,3-dimethylbutan-1-amine hydrochloride

Product 1

HCID 68854854N-(3,3-Dimethylbutyl)-N-ethyl-2-(3-isobutyryl-6-methoxy-1H-indazol-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Charge a 13×100 mm screw-capped tube with 27.6 mg (3-isobutyryl-6-methoxy-1H-indazol-1-yl)acetic acid, 23.0 mg HOBt hydrate, 18.6 mg N-ethyl-3,3-dimethylbutan-1-amine hydrochloride, and 89 μL DIEA. Dissolve the mixture in 1 mL anhydrous DMF. Add 38.3 mg EDC HCl salt and let the mixture sit at room temperature overnight. The title compound was isolated from the reaction mixture using RP-HPLC with 65-100% MeCN gradient with 0.1% TFA. LC-MS: 3.89 min. (m/Z=388.2, 410.1)

Workup

  1. additionCharge a 13×100 mm

Sources & evidence

ORD record
ord-bce0574aed2d4222b53431a1eb8c78d8
Source dataset
uspto-grants-2009_07
Patent number
US07563816B2

Reaction notes

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