1-Hydroxybenzotriazole → N-(3,3-dimethylbutyl)-2-[2-(2,2-dimethylpropanoyl)-5-methoxy-1-benzofuran-3-yl]-N-ethylacetamide

HRID 2103772Notes

Reaction equation

[CH3:1][C:2]([CH3:21])([CH3:20])[C:3]([C:5]1[O:6][C:7]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:8]=2[C:9]=1[CH2:10][C:11]([OH:13])=O)=[O:4].C1C=CC2N(O)N=NC=2C=1.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>CN(C=O)C.C(Cl)CCl>[CH3:39][C:38]([CH3:41])([CH3:40])[CH2:37][CH2:36][N:35]([CH2:33][CH3:34])[C:11](=[O:13])[CH2:10][C:9]1[C:8]2[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:7]=2[O:6][C:5]=1[C:3](=[O:4])[C:2]([CH3:1])([CH3:21])[CH3:20]

Participants

Conditions

Temperature: 45 °C

Procedure

To a mixture of 7.7 mg [2-(2,2-dimethylpropanoyl)-5-methoxy-1-benzofuran-3-yl]acetic acid from the Step B Example 1, 6.1 mg HOBt, and 10.2 mg EDC was added 0.5 mL dry DMF. Add 6.6 N-ethyl-3,3-dimethylbutan-1-amine hydrochloride from the Step A above followed by 16 μL DIEA. This solution was heated at 45° C. over night. It was purified directly on RP-HPLC using 65-80% MeCN gradient. The fractions containing pure product were pooled and lyophilized to give the title compound. LC-MS: 4.38 min. (m/Z=424.3, 318.2, 402.3).

Workup

customIt was purified directly on RP-HPLC using 65-80% MeCN gradient
additionThe fractions containing pure product

Sources & evidence

ORD record: ord-b9d0be350bb04a038b4ed91bfbf20a17
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576122B2

Reaction notes

Loading…