Benzoyl chloride → HCID 68706385, compound

HRID 889319Notes

Reaction equation

HRID 889319 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([N:11]2[C:15](=[O:16])[C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:13][NH:12]2)[CH:6]=1.C(N(CC)CC)C.[C:30]([Cl:38])(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C=O)C>[ClH:38].[O:16]=[C:15]1[N:11]([C:7]2[CH:6]=[C:5]([CH2:4][NH:3][C:30](=[O:37])[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:10]=[CH:9][N:8]=2)[NH:12][CH:13]=[C:14]1[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 68704213HCID 68704213, compound

Product 1

HCID 68706385HCID 68706385, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60.0 mg (176 μmol) of the compound from Example 35 are dissolved in 4 ml DMF, 53.5 mg (529 μmol) triethylamine and 27.3 mg (194 μmol) benzoyl chloride are added, while cooling with ice, and the mixture is stirred overnight at RT. The reaction mixture is purified directly by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% conc. hydrochloric acid).

Workup

  1. temperaturewhile cooling with ice
  2. customThe reaction mixture is purified directly by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% conc. hydrochloric acid)

Sources & evidence

ORD record
ord-f77a9f63dffa4a53b5e9dbb44dbe4167
Source dataset
uspto-grants-2012_08
Patent number
US08252817B2

Reaction notes

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