1-Hydroxybenzotriazole → 2-[3-(2,2-Dimethylpropanoyl)-6-methoxy-1H-indazol-1-yl]-N-ethyl-N-1,3-thiazol-2-ylacetamide

HRID 490809Notes

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](O)=[O:18])[N:6]=1)=[O:4].C1C=CC2N(O)N=NC=2C=1.[CH2:32]([NH:34][C:35]1[S:36][CH:37]=[CH:38][N:39]=1)[CH3:33].CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)CCl>[CH3:21][C:2]([CH3:1])([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]([N:34]([CH2:32][CH3:33])[C:35]2[S:36][CH:37]=[CH:38][N:39]=2)=[O:18])[N:6]=1)=[O:4]

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 19.2 mg N-ethyl-1,3-thiazol-2-amine 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 50-90% MeCN gradient. The pure product fractions were pooled and lyophilized to give the title compound as a white solid. LC-MS: 3.96 min. (m/Z=423.2, 245.1, 273.1, 401.2).

Workup

custompurified by RP-HPLC using 50-90% MeCN gradient

Sources & evidence

ORD record: ord-5f7fdec403bf48678c5e7bc19e148933
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528163B2

Reaction notes

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