Diisopropylethylamine → HCID 67966834, compound
Reaction equation
CCN(C(C)C)C(C)C.[CH3:10][C:11]([O:14][C:15]([NH:17][C@H:18]([CH2:22][CH3:23])[C:19]([OH:21])=O)=[O:16])([CH3:13])[CH3:12].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:46]([CH:48]1[C:52]2[C:53]([O:57][C:58]3[N:63]=[CH:62][C:61]([NH2:64])=[CH:60][CH:59]=3)=[CH:54][CH:55]=[CH:56][C:51]=2[CH2:50][O:49]1)[CH3:47]>CN(C)C=O>[CH2:46]([CH:48]1[C:52]2[C:53]([O:57][C:58]3[N:63]=[CH:62][C:61]([NH:64][C:19]([C@H:18]([NH:17][C:15](=[O:16])[O:14][C:11]([CH3:10])([CH3:12])[CH3:13])[CH2:22][CH3:23])=[O:21])=[CH:60][CH:59]=3)=[CH:54][CH:55]=[CH:56][C:51]=2[CH2:50][O:49]1)[CH3:47]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
In a 8 ml vial 6-[(3-ethyl-1,3-dihydro-2-benzofuran-4-yl)oxy]-3-pyridinamine (Intermediate 108, 10 mg) was dissolved in N,N-dimethylformamide (1 ml) to give a colourless solution. DIPEA (10.22 μl, 0.059 mmol), (2R)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)butanoic acid (9.52 mg, 0.047 mmol) and, finally, TBTU (15.03 mg, 0.047 mmol) were added. The reaction mixture was shaken at 60° C. After overnight shaking, the reaction was completed. The reaction mixture was evaporated under vacuum to give the crude product as a yellow oil which was purified via Biotage SP1 (with Cyclohexane/EtOAc as eluents from 2:1 to 1:1 in 10 CV; then 2:1 for 5 CV; 10 g SNAP Silica column). The collected fractions afforded the title compound as a colourless oil (12.7 mg).
Workup
- customto give a colourless solution
- stirringAfter overnight shaking
- customThe reaction mixture was evaporated under vacuum
- customto give the crude product as a yellow oil which
- customwas purified via Biotage SP1 (with Cyclohexane/EtOAc as eluents from 2:1 to 1:1 in 10 CV
Sources & evidence
- ORD record
- ord-03bb8348d8554e829b8d07bca7fcc910
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346790B2
Reaction notes
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