Hydrochloric Acid → HCID 11450628, compound

HRID 2056632Notes

Reaction equation

HRID 2056632 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 residue 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 residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-1c33426afb8f42f6a83ff22bfa06e448
Source dataset
uspto-grants-2008_02
Patent number
US07335676B2

Reaction notes

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