Dichloromethane → HCID 118023156, compound

HRID 929303Notes

Reaction equation

HRID 929303 reaction equation
Cl.Cl.ClC1[C:8]([N:9]([CH2:16][CH3:17])[C:10](=[O:15])[CH2:11][CH2:12][NH:13][CH3:14])=[CH:7][N:6]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[N:5]=1.CCN(C(C)C)C(C)C.[C:33](Cl)(=[O:35])[CH3:34].[CH2:37]([Cl:39])Cl>>[Cl:39][C:37]1[C:8]([N:9]([CH2:16][CH3:17])[C:10](=[O:15])[CH2:11][CH2:12][N:13]([CH3:14])[C:33](=[O:35])[CH3:34])=[CH:7][N:6]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[N:5]=1

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 118023895HCID 118023895, compound

Product 1

HCID 118023156HCID 118023156, compound

Procedure

To a stirred solution of N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-(methylamino) propanamide dihydrochloride (0.060 g, 0.16 mmol) in CH2Cl2 (0.5 mL) was added DIPEA (0.081 g, 0.60 mmol) followed by acetyl chloride (0.019 mg, 0.24 mmol). The reaction mixture was stirred for 16 hours. The reaction mixture was then diluted with CH2Cl2 and washed with water. The organic phase was separated, dried, concentrated, and then purified by silica gel chromatography eluting with 0%-10% MeOH/CH2Cl2 to afford the title compound F64 as a colorless oil (0.025 g, 45%).

Workup

  1. washwashed with water
  2. customThe organic phase was separated
  3. customdried
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography
  6. washeluting with 0%-10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-4b09a3d845744994828939d1b8090561
Source dataset
uspto-grants-2016_03
Patent number
US09295260B2

Reaction notes

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