Hydrochloric Acid → HCID 25138367, compound

HRID 1924804Notes

Reaction equation

HRID 1924804 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[N:11][CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH2:13]([C:16]1[CH:17]=[N:18][C:19]([N:22]2[CH2:27][CH2:26][CH:25]([O:28][C:29]3[CH:34]=[CH:33][NH:32][C:31](=[O:35])[CH:30]=3)[CH2:24][CH2:23]2)=[N:20][CH:21]=1)[CH2:14][CH3:15].N1C2C(=CC=CC=2O)C=CC=1.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.O.C(Cl)Cl.[Cu]I>[N:8]1([C:5]2[CH:6]=[CH:7][C:2]([N:32]3[CH:33]=[CH:34][C:29]([O:28][CH:25]4[CH2:26][CH2:27][N:22]([C:19]5[N:18]=[CH:17][C:16]([CH2:13][CH2:14][CH3:15])=[CH:21][N:20]=5)[CH2:23][CH2:24]4)=[CH:30][C:31]3=[O:35])=[CH:3][CH:4]=2)[CH:12]=[N:11][CH:10]=[N:9]1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 18980104HCID 18980104, compoundHCID 670725174-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one

Product 1

HCID 25138367HCID 25138367, compoundYield 32.8%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 1-(4-bromophenyl)-1H-1,2,4-triazole (45 mg, 0.20 mmol), 4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one (58 mg, 0.18 mmol), quinolin-8-ol (11 mg, 0.074 mmol, Alfa Aesar), potassium carbonate (33 mg, 0.24 mmol), Copper(I) iodide (14 mg, 0.074 mmol, Alfa Aesar) in DMSO (2 mL) was heated under microwave condition at 160° C. for 30 min. The resulting mixture was diluted with H2O and extracted with EtOAc (2×). The combined organic layers were concentrated in vacuo to a green oil. The oil was purified by flash chromatography (SiO2, 0 to 100% EtOAc in CH2Cl2 and then SiO2, 0 to 10% MeOH in CH2Cl2) to yield an off-white solid. The solid was dissolved in DCM and 1 eq of HCl (1N HCl in Et2O) was added, the resulting mixture stirred for 5 min and then concentrated in vacuo to give 27 mg of desired product as an off-white solid. MS (ESI) 458 (M+H).

Workup

  1. extractionextracted with EtOAc (2×)
  2. concentrationThe combined organic layers were concentrated in vacuo to a green oil
  3. customThe oil was purified by flash chromatography (SiO2, 0 to 100% EtOAc in CH2Cl2
  4. customSiO2, 0 to 10% MeOH in CH2Cl2) to yield an off-white solid
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0eb43cdaefff48188e430683a70b3bbd
Source dataset
uspto-grants-2012_05
Patent number
US08178561B2

Reaction notes

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