Acetyl chloride → HCID 68706447, compound

HRID 1526098Notes

Reaction equation

HRID 1526098 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:33])(=[O:32])[CH3:31]>CN(C=O)C>[ClH:33].[O:16]=[C:15]1[N:11]([C:7]2[CH:6]=[C:5]([CH2:4][NH:3][C:30](=[O:32])[CH3:31])[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 6367Acetyl chlorideHCID 8471TriethylamineHCID 68704213HCID 68704213, compound

Product 1

HCID 68706447HCID 68706447, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

80.0 mg (235 μmol) of the compound from Example 35 are dissolved in 5 ml DMF, 71.4 mg (705 μmol) triethylamine and 20.3 mg (259 μmol) acetyl 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-beb0b2fb86fa42708e8215e3f79d86f0
Source dataset
uspto-grants-2015_07
Patent number
US09085572B2

Reaction notes

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