1-Hydroxybenzotriazole → N-Butyl-2-[3-(2,2-dimethylpropanoyl)-6-methoxy-1H-indazol-1-yl]-N-propylacetamide

HRID 490808Notes

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:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:33][CH3:34].CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)CCl>[CH2:36]([N:35]([CH2:32][CH2:33][CH3:34])[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]([CH3:1])([CH3:21])[CH3:20])=[N:6]1)[CH2:37][CH2:38][CH3:39]

Participants

Conditions

Temperature: 45 °C

Procedure

Weigh 29.0 mg [3-(2,2-dimethylpropanoyl)-6-methoxy-1H-indazol-1-yl]acetic acid, 23.0 mg HOBt, and 38.3 mg EDC into a 13×100 mm screw cap tube. Add 17.3 mg N-propylbutylamine followed by 1 mL DMF and 45.2 mg DIEA in that order. The mixture was stirred at 45° C. for two hours 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=388.3, 410.3).

Workup

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

Sources & evidence

ORD record: ord-6a026c32192a43d69d32169d71ab4fd6
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528163B2

Reaction notes

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