Hydrochloric Acid → HCID 87732739, compound

HRID 132576Notes

Reaction equation

HRID 132576 reaction equation
Cl.Cl.[CH2:3]([N:10]([CH2:18][C:19]1([NH:22][CH3:23])[CH2:21][CH2:20]1)[C:11]1[CH:12]=[N:13][C:14]([Cl:17])=[CH:15][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:24]=O.Cl>C(O)=O.C(O)C.CCOCC>[ClH:17].[CH2:3]([N:10]([CH2:18][C:19]1([N:22]([CH3:24])[CH3:23])[CH2:20][CH2:21]1)[C:11]1[CH:12]=[N:13][C:14]([Cl:17])=[CH:15][CH:16]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 87733688HCID 87733688, compound

Product 1

HCID 87732739HCID 87732739, compound

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

3.1 g of the base of the compound of Example 17 are dissolved in 60 ml of formic acid. 60 ml of 37% aqueous formaldehyde solution are added and the mixture is heated for 4 hours at 70° C. Concentration to dryness is carried out, and the residue is taken up in 50% aqueous potassium carbonate solution and extraction is carried out with dichloromethane. The organic phase is dried over sodium sulphate, concentration is carried out, and the residue is chromatographed on silica gel (dichloromethane/acetone: 96/4). A fraction consisting of 0.48 g of base of the expected compound is isolated which, after dissolution in 5 ml of ethanol and addition of hydrochloric acid solution in ether, allows, after filtering off a precipitate and drying, 0.4 g of the expected compound to be obtained.

Workup

  1. concentrationConcentration to dryness
  2. extractionextraction
  3. dry with materialThe organic phase is dried over sodium sulphate, concentration
  4. customthe residue is chromatographed on silica gel (dichloromethane/acetone: 96/4)
  5. customis isolated which
  6. filtrationafter filtering off a precipitate
  7. customdrying

Sources & evidence

ORD record
ord-48a0aa145fb647fbb94c6270cfa52a06
Source dataset
uspto-grants-2008_06
Patent number
US07388022B2

Reaction notes

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