Butylethylamine → HCID 11406165, compound

HRID 2103757Notes

Reaction equation

HRID 2103757 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.[CH2:32]([NH:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH3:33].CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)CCl>[CH2:35]([N:34]([CH2:32][CH3:33])[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]([CH3:21])([CH3:20])[CH3:1])[CH2:36][CH2:37][CH3:38]

Participants

7

Reactant 4

HCID 25914ButylethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57804476[2-(2,2-Dimethylpropanoyl)-5-methoxy-1-benzofuran-3-yl]acetic acid

Product 1

HCID 11406165HCID 11406165, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

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 12.0 μL N-ethylbutylamine 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 60-100% MeCN gradient. The fractions containing pure product were pooled and lyophilized to give the title compound. LC-MS: 4.15 min. (m/Z=290.1, 374.2, 396.1).

Workup

  1. dissolutionDissolve
  2. customIt was purified directly on RP-HPLC using 60-100% MeCN gradient
  3. additionThe fractions containing pure product

Sources & evidence

ORD record
ord-7a86bc9dff394bc3a40558d9840b800a
Source dataset
uspto-grants-2009_08
Patent number
US07576122B2

Reaction notes

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