trans-N,N'-dimethyl-1,2-cyclohexanediamine → HCID 71042406, compound

HRID 925613Notes

Reaction equation

HRID 925613 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:10]=[C:11]3[C:16](=[C:17]4[N:22]([CH3:23])[CH2:21][CH:20]=[CH:19][C:18]=24)[N:15]=[CH:14][N:13]([C@H:24]2[CH2:29][CH2:28][CH2:27][CH2:26][C@@H:25]2[OH:30])[C:12]3=[O:31])=[CH:4][CH:3]=1.CN[C@@H]1CCCC[C@H]1NC>CO.[Cu]I>[OH:30][C@H:25]1[CH2:26][CH2:27][CH2:28][CH2:29][C@@H:24]1[N:13]1[C:12](=[O:31])[C:11]2[C:16](=[C:17]3[N:22]([CH3:23])[CH2:21][CH:20]=[CH:19][C:18]3=[C:9]([CH2:8][C:5]3[CH:6]=[N:7][CH:2]=[CH:3][CH:4]=3)[CH:10]=2)[N:15]=[CH:14]1

Participants

5

Reactant 2

HCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 71472666HCID 71472666, compound

Product 1

HCID 71042406HCID 71042406, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 6-[(6-chloropyridin-3-yl)methyl]-3-[(1S,2S)-2-hydroxycyclohexyl]-10-methyl-9,10-dihydropyrido[3,2-h]quinazolin-4(3H)-one (Example 1, 0.050 g, 0.11 mmol) in 1 mL of methanol under an atmosphere of nitrogen was added trans-N,N′-dimethylcyclohexane-1,2-diamine (1.6 mg, 0.011 mmol) and copper(I) iodide (2.2 mg, 0.011 mmol). The mixture was heated at 160° C. for 2 h in a sealed pressure vessel, cooled to rt, and concentrated in vacuo. The residue was purified via preparative reverse phase HPLC to provide the title compounds.

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified via preparative reverse phase HPLC

Sources & evidence

ORD record
ord-f2886afe83aa4c3589e85d128b00b66d
Source dataset
uspto-grants-2016_03
Patent number
US09284312B2

Reaction notes

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