Benzoyl chloride → HCID 22245786, compound

HRID 890624Notes

Reaction equation

HRID 890624 reaction equation
[NH2:1][C:2]1[C:3]([CH3:22])=[C:4]([C:17]([CH3:21])=[CH:18][C:19]=1[CH3:20])[NH:5][CH2:6][C:7]([N:9]([CH3:16])[CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)=[O:8].[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C>C(Cl)Cl>[NH2:1][C:2]1[C:3]([CH3:22])=[C:4]([C:17]([CH3:21])=[CH:18][C:19]=1[CH3:20])[NH:5][CH2:6][C:7]([N:9]([CH:10]1[CH2:15][CH2:14][N:13]([C:23](=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:12][CH2:11]1)[CH3:16])=[O:8]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 22245729HCID 22245729, compound

Product 1

HCID 22245786HCID 22245786, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture solution of 300 mg of the compound (23) obtained in the Example 23, 114 μl of benzoyl chloride and 206 μl of triethylamine in 5 ml of methylene chloride were stirred for 2 hoursat 0° C. After the reaction, the solvent was removed and the obtained residue was purified by amine-coated silica gel (Fuji Silysia Chemical Ltd.; NH-DM1020) column chromatography (methylene chloride:ether=1:1) to give the above-mentioned compound (128) in 66% yield.

Workup

  1. customAfter the reaction
  2. customthe solvent was removed
  3. customthe obtained residue was purified by amine-coated silica gel (Fuji Silysia Chemical Ltd.; NH-DM1020) column chromatography (methylene chloride:ether=1:1)

Sources & evidence

ORD record
ord-d3d83cbfc79344b0b246900e6ddff52c
Source dataset
uspto-grants-2006_02
Patent number
US06998401B2

Reaction notes

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