Hydrochloric Acid → HCID 11450628, compound

HRID 1243634Notes

Reaction equation

HRID 1243634 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COCCOC[N:16]1[C:20]2[CH:21]=[CH:22][C:23]([NH2:33])=[C:24]3[C:25](=[O:32])[C:26]4[C:31]([C:18]([C:19]=23)=[N:17]1)=[CH:30][CH:29]=[CH:28][CH:27]=4.C(N(CC)CC)C.Cl>C(Cl)Cl>[C:1]([NH:33][C:23]1[CH:22]=[CH:21][C:20]2[NH:16][N:17]=[C:18]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:25](=[O:32])[C:24]=1[C:19]=23)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 21064960HCID 21064960, compound

Product 1

HCID 11450628HCID 11450628, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Benzoyl chloride is added to a solution of 2-(methoxyethoxymethyl)-5-aminoanthra[1,9cd]pyrazol-6-(2H)one and triethylamine in methylene chloride at 0° C. The mixture is stirred for 16 hours, quenched with water, and extracted with ethyl acetate (×2). The combined organic layer is washed with sodium bicarbonate solution, and brine, dried and evaporated. The crude reaction mixture is then taken in aqueous 6N hydrochloric acid, and heated at 80° C. for 4 hours. After cooling, the mixture is extracted with ethyl acetate (×2), washed with brine, dried, and evaporated. The reside is chromatographed on silica gel to furnish the desired amide as a yellow solid.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate (×2)
  3. washThe combined organic layer is washed with sodium bicarbonate solution, and brine
  4. customdried
  5. customevaporated
  6. customThe crude reaction mixture
  7. temperatureAfter cooling
  8. extractionthe mixture is extracted with ethyl acetate (×2)
  9. washwashed with brine
  10. customdried
  11. customevaporated
  12. customThe reside is chromatographed on silica gel

Sources & evidence

ORD record
ord-b162505eac354676bec258b3785fb9d6
Source dataset
uspto-grants-2006_10
Patent number
US07119114B1

Reaction notes

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