Triethylamine → HCID 70561773, compound

HRID 1427224Notes

Reaction equation

HRID 1427224 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:14]2[C:22]3[C:17](=[C:18]([N:23]4C(C)=CC=C4C)[CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15]2)([CH2:12][CH3:13])[CH2:9][O:10][CH3:11])=[CH:4][CH:3]=1.NO.Cl.C(N(CC)CC)C>C(O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:14]2[C:22]3[CH:21]=[CH:20][CH:19]=[C:18]([NH2:23])[C:17]=3[CH:16]=[CH:15]2)([CH2:12][CH3:13])[CH2:9][O:10][CH3:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 70562743HCID 70562743, compound

Product 1

HCID 70561773HCID 70561773, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To the mixture of 1-(2-(4-chlorophenyl)-1-methoxybutan-2-yl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)-1H-indole (70 mg) in ethanol/H2O (3 mL/1 mL) was added NH2OH—HCl (178 mg) and triethylamine (87 mg) and the reaction mixture was refluxed for 18 h in an oil bath, cooled to room temperature, concentrated, and extracted with ethyl acetate (30 mL). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified using a silica gel column (20-40% ethyl acetate in hexane) to afford the title compound as a brown solid. LC/MS m/z=329.1 [M+H]+.

Workup

  1. temperaturethe reaction mixture was refluxed for 18 h in an oil bath
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate (30 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified

Sources & evidence

ORD record
ord-d3e341cde96745c396186f8b8c395bcc
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

Loading…