Methylhydrazine → HCID 57650326, compound

HRID 2063490Notes

Reaction equation

HRID 2063490 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C:7](=[CH:22][N:23](C)[CH3:24])[C:8]([C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=O)=[CH:4][CH:3]=1.C[NH:29]N>C(O)C>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C:7]2[C:8]([C@H:10]3[CH2:14][CH2:13][CH2:12][N:11]3[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[N:29][N:23]([CH3:24])[CH:22]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 68811060HCID 68811060, compound

Product 1

HCID 57650326HCID 57650326, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (R)-tert-butyl 2-(2-(4-chlorobenzyl)-3-(dimethylamino)acryloyl)pyrrolidine-1-carboxylate (120 mg, 0.3 mmol) in ethanol (4 mL) was added 1-methylhydrazine (60 μL, 2.4 mmol). The resulting solution was heated at 70° C. for 3 h and concentrated in vacuo. Purification of the resulting residue by silica gel column chromatography (hexanes/ethyl acetate gradient, 10-100% ethyl acetate) afforded (R)-tert-butyl 2-(4-(4-chlorobenzyl)-1-methyl-1H-pyrazol-3-yl)pyrrolidine-1-carboxylate (78 mg, 75%). LCMS: calculated: 375, found (MH+): 376.

Workup

  1. concentrationconcentrated in vacuo
  2. customPurification of the resulting residue by silica gel column chromatography (hexanes/ethyl acetate gradient, 10-100% ethyl acetate)

Sources & evidence

ORD record
ord-a1416fb39ee64cf1bbb34ed146777e40
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

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