Propionyl chloride → HCID 59425487, compound

HRID 502253Notes

Reaction equation

HRID 502253 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:26][CH3:27])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([N:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)[CH:11]=3)=[CH:4][CH:3]=1.[C:28](Cl)(=[O:31])[CH2:29][CH3:30]>N1C=CC=CC=1>[C:17]([C:16]1[C:15]2[C:10](=[CH:11][C:12]([N:19]3[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]3)=[CH:13][CH:14]=2)[N:9]([CH2:26][CH3:27])[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:28](=[O:31])[CH2:29][CH3:30])=[CH:3][CH:4]=1)#[N:18]

Participants

4

Reactant 2

HCID 62324Propionyl chlorideHCID 59425294HCID 59425294, compound

Product 1

HCID 59425487HCID 59425487, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of the compound obtained in step B (54 mg, 0.15 mmol) in dry pyridine (1.5 mL) is added propionyl chloride (26 μL, 0.30 mmol). The mixture is stirred at room temperature overnight and the solvent is removed in vacuo. The residue is dissolved with DCM (5 mL) and washed with water (2×4 mL) and chromatographed (silica gel, MeOH/DCM, 0.5/9.5) to provide product, {N-{4-[3-cyano-1-ethyl-6-(4-methylpiperazin-1-yl)indol-2-yl]phenyl}propionamide (45 mg, 73%).

Workup

  1. customthe solvent is removed in vacuo
  2. dissolutionThe residue is dissolved with DCM (5 mL)
  3. washwashed with water (2×4 mL)
  4. customchromatographed (silica gel, MeOH/DCM, 0.5/9.5)

Sources & evidence

ORD record
ord-990d14f1b084452c9d69dd35bcf30228
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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