Dimethylcarbamoyl Chloride → 1-((3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)(ethyl)amino)-1-oxopropan-2-yl dimethylcarbamate

HRID 929306Notes

Reaction equation

HRID 929306 reaction equation
[Cl:1][C:2]1[C:6]([N:7]([CH2:13][CH3:14])[C:8](=[O:12])[CH:9]([OH:11])[CH3:10])=[CH:5][N:4]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[N:3]=1.[CH3:21][N:22]([CH3:26])[C:23](Cl)=[O:24]>C(Cl)Cl>[CH3:21][N:22]([CH3:26])[C:23](=[O:24])[O:11][CH:9]([CH3:10])[C:8]([N:7]([C:6]1[C:2]([Cl:1])=[N:3][N:4]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:5]=1)[CH2:13][CH3:14])=[O:12]

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 86700598N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-2-hydroxypropanamide

Product 1

HCID 1180239331-((3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)(ethyl)amino)-1-oxopropan-2-yl dimethylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-2-hydroxypropanamide (0.10 g, 0.34 mmol) in CH2Cl2 (1.1 mL) was added dimethylcarbamic chloride (0.073 g, 0.68 mmol). The reaction mixture was stirred at room temperature for 16 hours, and then diluted with CH2Cl2, washed with water. The phases were separated, dried and concentrated. The residue was purified by basic alumina gel chromatography eluting with 0%-70% acetone/hexanes to afford the title compound F93 as a light yellow oil (0.11 g, 87%).

Workup

  1. washwashed with water
  2. customThe phases were separated
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by basic alumina gel chromatography
  6. washeluting with 0%-70% acetone/hexanes

Sources & evidence

ORD record
ord-d8b0aa2acb7d496db740ba7a700c3e45
Source dataset
uspto-grants-2016_03
Patent number
US09295260B2

Reaction notes

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