Acetyl chloride → HCID 22064704, compound

HRID 1828079Notes

Reaction equation

HRID 1828079 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[CH:11][N:10]([CH:13]([O:26][CH2:27][CH3:28])[C:14]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=3)=[O:15])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:36](Cl)(=[O:38])[CH3:37]>ClCCl.CCOC(C)=O>[C:36]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[CH:11][N:10]([CH:13]([O:26][CH2:27][CH3:28])[C:14]([NH:16][CH2:17][C:18]3[CH:19]=[CH:20][C:21]([C:24]#[N:25])=[CH:22][CH:23]=3)=[O:15])[N:9]=2)[CH:5]=[CH:6][CH:7]=1)(=[O:38])[CH3:37]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 22064707HCID 22064707, compound

Product 1

HCID 22064704HCID 22064704, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred, cooled (0° C.) solution of (RS)-2-[3-(3-amino-phenyl)-pyrazol-1-yl]-N-(4-cyano-benzyl)-2-ethoxy-acetamide (117 mg, example 5.2) in dichloromethane (5 ml) under an argon atmosphere were added triethylamine (0.06 ml) and acetyl chloride (0.02 ml). Stirring at 0° C. was continued for 3 hrs. The mixture was diluted with EtOAc, washed with 1.0 N HCl and brine, dried (MgSO4), filtered and concentrated. The crude product was isolated by chromatography (silica gel, gradient CH2Cl2 to CH2Cl2/MeOH 9:1) to give 2-[3-(3-acetylamino-phenyl)-pyrazol-1-yl]-N-(4-cyano-benzyl)-2-ethoxy-acetamide (115 mg) as off-white solid. MS 418.2 ([M+H]+)

Workup

  1. washwashed with 1.0 N HCl and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was isolated by chromatography (silica gel, gradient CH2Cl2 to CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-0fd27d0f114145aea25f8631d8bcb9d1
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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