N-Ethyl cyclohexylamine → N-cyclohexyl-2-[2-(2,2-dimethylpropanoyl)-5-methoxy-1-benzofuran-3-yl]-N-ethylacetamide

HRID 2103755Notes

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](O)=[O:12])=[O:4].C1C=CC2N(O)N=NC=2C=1.[CH2:32]([NH:34][CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)[CH3:33].CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)CCl>[CH:35]1([N:34]([CH2:32][CH3:33])[C:11](=[O:12])[CH2:10][C:9]2[C:8]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:7]=3[O:6][C:5]=2[C:3](=[O:4])[C:2]([CH3:1])([CH3:20])[CH3:21])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

Conditions

Temperature: 40 °C

Procedure

Dissolve a mixture of 17 mg [2-(2,2-dimethylpropanoyl)-5-methoxy-1-benzofuran-3-yl]acetic acid from the Step B Example 1 and 18.5 mg HOBt in 1 mL dry DMF. Add 13.2 μL N-ethylcyclohexylamine followed by 23.0 mg EDC and 35 μL DIEA. This solution was heated at 40° C. for 2 hours. It was purified directly on RP-HPLC using 65-100% MeCN gradient. The fractions containing pure product were pooled and lyophilized to give the title compound. LC-MS: 4.34 min. (m/Z=400.2, 422.1, 316.1).

Workup

dissolutionDissolve
customIt was purified directly on RP-HPLC using 65-100% MeCN gradient
additionThe fractions containing pure product

Sources & evidence

ORD record: ord-5ee7cc99e42b409f9ca0471f9189dbfd
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576122B2

Reaction notes

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