Benzoyl chloride → HCID 68706385, compound

HRID 1526099Notes

Reaction equation

HRID 1526099 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-ada8cd6c94a64de782455e544a6114c1
Source dataset
uspto-grants-2015_07
Patent number
US09085572B2

Reaction notes

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