Bis(2-oxo-3-oxazolidinyl)phosphinic chloride → 2-(3,4,5,6-Tetrahydro-2H-[1,4']bipyridyl-4-ylcarbamoyl)-1H-pyrrolo[3,2-b]pyridine-5-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:10]=[C:9]2[CH:11]=[C:12]([C:14]([OH:16])=O)[NH:13][C:8]2=[CH:7][CH:6]=1)=[O:4].Cl.Cl.[N:19]1([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[CH2:24][CH2:23][CH:22]([NH2:25])[CH2:21][CH2:20]1.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>ClCCl.C(N(CC)CC)C>[CH3:1][O:2][C:3]([C:5]1[N:10]=[C:9]2[CH:11]=[C:12]([C:14](=[O:16])[NH:25][CH:22]3[CH2:21][CH2:20][N:19]([C:26]4[CH:27]=[CH:28][N:29]=[CH:30][CH:31]=4)[CH2:24][CH2:23]3)[NH:13][C:8]2=[CH:7][CH:6]=1)=[O:4]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 450 mg 1H-pyrrolo[3,2-b]pyridine-2,5-dicarboxylic acid 5-methyl ester in 9 mL dichloromethane and 1.13 mL triethylamine, 614 mg 3,4,5,6-tetrahydro-2H-[1,4′]bipyridyl-4-ylamine dihydrochloride and 520 mg bis(2-oxo-3-oxazolidinyl)phophinic chloride were added at room temperature and the mixture was stirred for 2 hours. After treatment of the reaction mixture with 5 mL saturated aqueous solution of potassium carbonate the precipitate was collected by filtration and coevaporated twice with toluene. The residue was directly subjected to the subsequent reaction without further purification.
Workup
- filtrationAfter treatment of the reaction mixture with 5 mL saturated aqueous solution of potassium carbonate the precipitate was collected by filtration
- customThe residue was directly subjected to the subsequent reaction without further purification
Sources & evidence
- ORD record
- ord-ad26f16d3bb240138f1435f7fd84a9e1
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07317027B2
Reaction notes
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