Dimethylformamide → HCID 44226452, compound

HRID 1947125Notes

Reaction equation

HRID 1947125 reaction equation
[CH3:1][O:2][C:3]1[C:7]2[C:8](=[O:25])[N:9]([CH2:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]=2[N:5]([CH3:26])[C:4]=1[C:27]([NH:29][CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)=[O:28].Br[CH2:37][CH2:38][OH:39].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[OH:39][CH2:38][CH2:37][N:33]1[CH2:32][CH2:31][CH:30]([NH:29][C:27]([C:4]2[N:5]([CH3:26])[C:6]3[C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[N:9]([CH2:16][C:17](=[O:24])[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:8](=[O:25])[C:7]=3[C:3]=2[O:2][CH3:1])=[O:28])[CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 57860479HCID 57860479, compound

Product 1

HCID 44226452HCID 44226452, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the compound of Example 77 (200 mg, 0.399 mmol), 2-bromoethanol (42.5 μL, 0.599 mmol), potassium carbonate (248 mg, 1.80 mmol) and DMF (5 mL) was stirred at 100° C. for 15 hr. The reaction mixture was diluted with water, and extracted twice with ethyl acetate. The extract was combined, washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by aminosilica gel chromatography (eluate; ethyl acetate), and the obtained solid was recrystallized from ethyl acetate-ethanol to give the title compound (68.0 mg, 33%) as white crystals.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by aminosilica gel chromatography (eluate; ethyl acetate)
  6. customthe obtained solid was recrystallized from ethyl acetate-ethanol

Sources & evidence

ORD record
ord-e5724a2b009c4915b499d581cd0dfef6
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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