Imidazole → HCID 44218880, compound

HRID 1931511Notes

Reaction equation

HRID 1931511 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][C@H:13]1[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14]1)[CH:6]=[CH:5]2.[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1.C(C1CCCCC1=O)(=O)C.C(=O)([O-])[O-].[K+].[K+]>[Cu]Cl.O.CN1CCCC1=O>[N:22]1([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[C:7]([NH:12][C@H:13]2[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:15][CH2:14]2)[CH:6]=[CH:5]3)[CH:26]=[CH:25][N:24]=[CH:23]1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 134002-AcetylcyclohexanoneHCID 57860971HCID 57860971, compound

Product 1

HCID 44218880HCID 44218880, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of (6-bromo-quinolin-2-yl)-(R)-indan-1-yl-amine (see example 53, step A) (339 mg, 1.0 mmol), commercially available imidazole (136 mg, 2.0 mmol), copper(I)chloride (10 mg, 0.1 mmol), 2-acetyl-cyclohexanone (35 mg, 0.25 mmol), potassium carbonate (145 mg, 1.05 mmol) and 1-methyl-2-pyrrolidone (1 ml) was heated in a sealed tube at 130° C. for 18 h. The reaction mixture was poured into water (20 ml) and extracted with ethyl acetate (2×30 ml). The combined organic layers were washed with saturated sodium bi-carbonate solution (2×20 ml) and brine (20 ml), dried (MgSO4) and evaporated. Further purification of the crude product by flash chromatography on silica gel (ethyl acetate/heptane) yielded the title compound (186 mg, 57%) as off-white foam.

Workup

  1. extractionextracted with ethyl acetate (2×30 ml)
  2. washThe combined organic layers were washed with saturated sodium bi-carbonate solution (2×20 ml) and brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customFurther purification of the crude product by flash chromatography on silica gel (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-93c27f52ffd948e8aca376dd6eaa04b5
Source dataset
uspto-grants-2012_05
Patent number
US08188284B2

Reaction notes

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