Diisopropylethylamine → HCID 178459998, compound
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:17])[C:12](=[CH2:16])[C:13]([OH:15])=O)=[CH:7][CH:6]=1)=[O:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:42][C:43]1[C:48]([Br:49])=[CH:47][CH:46]=[CH:45][N+:44]=1[O-:50].C(N(C(C)C)CC)(C)C>CN(C=O)C>[Br:49][C:48]1[C:43]([NH:42][C:13](=[O:15])[C:12](=[CH2:16])[CH:11]([C:8]2[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:10][CH:9]=2)[CH3:17])=[N+:44]([O-:50])[CH:45]=[CH:46][CH:47]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 23 °C
Procedure
A mixture of 3-(4-(methoxycarbonyl)phenyl)-2-methylenebutanoic acid (1.0 g, 4.2 mmol), HATU (1.9 g, 5.1 mmol), 2-amino-3-bromopyridine 1-oxide (0.88 g, 4.6 mmol) and diisopropyl ethylamine (2.22 mL, 12.5 mmol) in anhydrous DMF (10 mL) was stirred at 23° C. for 1 h, then concentrated. The residue was partitioned between ethyl acetate and brine (2×). The combined organic layers were dried over anhydrous sodium sulfate, and concentrated. The residue was triturated with acetonitrile (20 mL). The solid was filtered and dried under vacuum to give the title compound. MS: m/z=406.0 (M+1).
Workup
- concentrationconcentrated
- customThe residue was partitioned between ethyl acetate and brine (2×)
- dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
- concentrationconcentrated
- customThe residue was triturated with acetonitrile (20 mL)
- filtrationThe solid was filtered
- customdried under vacuum
Sources & evidence
- ORD record
- ord-c914242757004a578e545691f262b725
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296750B2
Reaction notes
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