Hydrochloric Acid → HCID 11175169, compound

HRID 2056633Notes

Reaction equation

HRID 2056633 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][CH:23]=[C:24]3[C:25](=[O:33])[C:26]4[C:31]([C:18]([C:19]=23)=[N:17]1)=[CH:30][CH:29]=[CH:28][C:27]=4[NH2:32].C(N(CC)CC)C.Cl>C(Cl)Cl>[C:1]([NH:32][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]2[C:26]=1[C:25](=[O:33])[C:24]1[C:19]3[C:18]2=[N:17][NH:16][C:20]=3[CH:21]=[CH:22][CH:23]=1)(=[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 21064961HCID 21064961, compound

Product 1

HCID 11175169HCID 11175169, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Benzoyl chloride is added to a solution of 2-(methoxyethoxymethyl)-7-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-f57ff51ca8d94ba592b14161ffb73fef
Source dataset
uspto-grants-2008_02
Patent number
US07335676B2

Reaction notes

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