Isopropylamine → 1-(5-Iodo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropanecarboxylic acid isopropylamide
Reaction equation
[I:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3([C:14]([OH:16])=O)[CH2:13][CH2:12]3)[N:10]=[C:6]2[C:5]([O:17][CH3:18])=[CH:4][CH:3]=1.CCN(CC)CC.CN(C(ON1N=[N:41][C:36]2[CH:37]=CC=N[C:35]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N)(C)C>CN(C=O)C.O>[CH:36]([NH:41][C:14]([C:11]1([C:9]2[N:10]=[C:6]3[C:5]([O:17][CH3:18])=[CH:4][CH:3]=[C:2]([I:1])[N:7]3[N:8]=2)[CH2:12][CH2:13]1)=[O:16])([CH3:37])[CH3:35]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Under an argon atmosphere 1-(5-Iodo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropanecarboxylic acid (compound 306) (0.05 g, 0.14 mmol) was dissolved in DMF (0.5 mL) and Et3N (0.058 mL, 0.42 mmol). HATU (0.082 g, 0.21 mmol) and isopropyl amine (0.018 mL, 0.21 mmol) were added. The solution was stirred at rt for 2 h. H2O was added and the aqueous phase was extracted with EtOAc (×3). The combined organic phases were washed with H2O and brine and dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica using DCM:EtOAc 9:1->3:1 as eluent. The title compound was obtained as a solid.
Workup
- extractionthe aqueous phase was extracted with EtOAc (×3)
- washThe combined organic phases were washed with H2O and brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude product was purified by flash chromatography on silica
Sources & evidence
- ORD record
- ord-7e426ed8d75e4e378c1cc4635b629e82
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952162B2
Reaction notes
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