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

HRID 2103769Notes

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.[CH3:33][C:34]([CH3:39])([CH3:38])[CH2:35][CH2:36][NH2:37].CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)CCl>[CH3:33][C:34]([CH3:39])([CH3:38])[CH2:35][CH2:36][NH:37][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]([CH3:20])([CH3:1])[CH3:21]

Participants

Conditions

Temperature: 45 °C

Procedure

To a mixture of 29 mg [2-(2,2-dimethylpropanoyl)-5-methoxy-1-benzofuran-3-yl]acetic acid from the Step B Example 1, 23 mg HOBt, and 38.3 mg EDC was added 1 mL dry DMF. Add 24.9 mg (3,3-dimethylbutyl)amine hydrochloride followed by 61 μL DIEA. This solution was heated at 45° C. for 2 hours. It was purified directly on RP-HPLC using 60-75% MeCN gradient. The fractions containing pure product were pooled and lyophilized to give the title compound. LC-MS: 4.08 min. (m/Z=290.1, 374.2, 396.2).

Workup

customIt was purified directly on RP-HPLC using 60-75% MeCN gradient
additionThe fractions containing pure product

Sources & evidence

ORD record: ord-6552561b9ccc42928a1e4f6d50ed9a22
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576122B2

Reaction notes

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