Triethylamine → n-{4-[4-(Methylamino)-3-nitrophenoxy](2-pyridyl)}[(2-morpholin-4-ylethyl)amino]carboxamide
Reaction equation
[CH3:1][NH:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10](C(O)=O)[CH:9]=2)=[CH:5][C:4]=1[N+:19]([O-:21])=[O:20].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.C([N:41]([CH2:44]C)CC)C.[N:46]1([CH2:52][CH2:53][NH2:54])[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1>C1(C)C=CC=CC=1>[CH3:1][NH:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:41][C:44]([NH:54][CH2:53][CH2:52][N:46]3[CH2:51][CH2:50][O:49][CH2:48][CH2:47]3)=[O:29])[CH:9]=2)=[CH:5][C:4]=1[N+:19]([O-:21])=[O:20]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
A flame dried flask was charged with 4-[4-(methylamino)-3-nitrophenoxy]-pyridine-2-carboxylic acid (1 eq), diphenylphosphoryl azide (1.1 eq), triethylamine (2.1 eq) and 20 ml toluene and heated for one and one half hours at 75° C. To this was added 2-morpholin-4-ylethylamine (1.2 eq) and the resulting mixture was stirred at 75° C. overnight. The reaction was then concentrated and partitioned between ethyl acetate and distilled water. The organic layer was dried with sodium sulfate and concentrated and titurated with ether then hexanes to give the purified product. MS: MH+=417.
Workup
- customA flame dried flask
- concentrationThe reaction was then concentrated
- custompartitioned between ethyl acetate
- distillationdistilled water
- dry with materialThe organic layer was dried with sodium sulfate
- concentrationconcentrated
- customhexanes to give the purified product
Sources & evidence
- ORD record
- ord-3cf4e63b45724422b2cfe7696403c629
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07423150B2
Reaction notes
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