Potassium Carbonate → HCID 58504305, compound

HRID 2407794Notes

Reaction equation

HRID 2407794 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3[S:28][C:27](Br)=[N:26][CH:25]=3)[CH2:19][CH2:18]2)=[O:14])[CH:3]=1.[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[OH:36].CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cu]I>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3[S:28][C:27]([N:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]4=[O:36])=[N:26][CH:25]=3)[CH2:19][CH2:18]2)=[O:14])[CH:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 58504093HCID 58504093, compoundHCID 178516071HCID 178516071, compound

Product 1

HCID 58504305HCID 58504305, compoundYield 35.6%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

The compound prepared in Example 336 (30 mg), pyridin-2-ol (0.0124 g), copper(I) iodide (0.0068 g), trans-N1,N2-dimethylcyclohexane-1,2-diamine (0.0113 mL), and potassium carbonate (0.0173 g) were combined in N,N-dimethylformamide (0.5 mL). The reaction mixture was purged with argon for 5 minutes and then heated at 110° C. for 4 hours. The reaction mixture was diluted with ethyl acetate (15 mL) and passed through a plug of silica gel, eluting with ethyl acetate. The eluent was concentrated and the residue was purified by column chromatography on silica gel (ethyl acetate:methanol=19:1) to obtain the title compound (11 mg) having the following physical data.

Workup

  1. customThe reaction mixture was purged with argon for 5 minutes
  2. additionThe reaction mixture was diluted with ethyl acetate (15 mL)
  3. washeluting with ethyl acetate
  4. concentrationThe eluent was concentrated
  5. customthe residue was purified by column chromatography on silica gel (ethyl acetate:methanol=19:1)

Sources & evidence

ORD record
ord-971cfb4915ab41448912ec5352053b17
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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