Triethylamine → HCID 178433121, compound

HRID 2117394Notes

Reaction equation

HRID 2117394 reaction equation
Cl.[NH2:2][CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]([CH3:6])=O.[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=1[NH:21][C:22]#[N:23].C(N(CC)CC)C>C(O)C>[ClH:13].[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=1[NH:21][C:22]1[NH:2][C:3]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:4]([CH3:6])[N:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27970031-amino-1-phenylpropan-2-one hydrochlorideHCID 12448337HCID 12448337, compound

Product 1

HCID 178433121HCID 178433121, compoundYield 14.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Amino-1-phenylacetone hydrochloride (189 mg), 2,6-dichlorophenylcyanamide (187 mg, prepared as described in J. Med. Chem., 1975, 18, 90-99) and triethylamine (101 mg) were kept at the reflux temperature in ethanol (10 ml) for 3 hours. Cooling was followed by drying in vacuo and purification by preparative HPLC. The product-containing fractions were combined, the acetonitrile was stripped in a rotary evaporator, and the aqueous residue was neutralized with potassium carbonate and extracted three times with ethyl acetate. Drying over magnesium sulfate was followed by evaporation to dryness and, after addition of hydrochloric acid, freeze drying. 26 mg of the title compound were obtained.

Workup

  1. temperatureCooling
  2. customby drying in vacuo and purification by preparative HPLC
  3. customthe acetonitrile was stripped in a rotary evaporator
  4. extractionextracted three times with ethyl acetate
  5. dry with materialDrying over magnesium sulfate
  6. customwas followed by evaporation to dryness
  7. additionafter addition of hydrochloric acid, freeze
  8. customdrying

Sources & evidence

ORD record
ord-9138ef6a672e4cecbcf2af8944c9e6bb
Source dataset
uspto-grants-2008_10
Patent number
US07442717B2

Reaction notes

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