Diisopropylethylamine → HCID 67356631, compound

HRID 1666009Notes

Reaction equation

HRID 1666009 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][NH:11][CH2:10][C@H:9]2[C:13]([O:15][CH3:16])=[O:14])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.Cl[C:27]1[N:28]=[N:29][C:30]([CH3:33])=[CH:31][CH:32]=1>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][N:11]([C:27]3[N:28]=[N:29][C:30]([CH3:33])=[CH:31][CH:32]=3)[CH2:10][C@H:9]2[C:13]([O:15][CH3:16])=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2272543-Chloro-6-methylpyridazineHCID 17998812HCID 17998812, compound2×

Product 1

HCID 67356631HCID 67356631, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The product of Step A, methyl (3S,4R)-4-(4-chlorophenyl)pyrrolidine-3-carboxylate (0.46 g, 1.92 mmol) was dissolved in dioxane (2 ml). DIPEA (1.34 ml, 7.67 mmol) and 3-chloro-6-methylpyridazine (0.74 g, 5.76 mmol) were added. The reaction was conducted at 180° C. for 5 minutes with microwave. Then, the reaction mixture was concentrated in vacuo. EtOAc was added to the obtained residue. The mixture was diluted with EtOAc, washed with water and purified by column chromatography (eluent: EtOAc/Hex=1/2) to give the title compound (0.48 g, 75%).

Workup

  1. concentrationThen, the reaction mixture was concentrated in vacuo
  2. additionEtOAc was added to the obtained residue
  3. additionThe mixture was diluted with EtOAc
  4. washwashed with water
  5. custompurified by column chromatography (eluent: EtOAc/Hex=1/2)

Sources & evidence

ORD record
ord-7c1030d8414f4dea9e038b0be32b420d
Source dataset
uspto-grants-2011_10
Patent number
US08039622B2

Reaction notes

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