Hydrochloric Acid → HCID 178456462, compound

HRID 1292424Notes

Reaction equation

HRID 1292424 reaction equation
[CH2:1]([N:4]1[C:13](=[O:14])[C:12]2[NH:11][C:10](/[CH:15]=[CH:16]/[C:17]3[N:18](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:19]=[N:20][CH:21]=3)=[N:9][C:8]=2[N:7]([CH2:41][CH2:42][CH3:43])[C:5]1=[O:6])[CH2:2][CH3:3].Cl.[CH3:45]O>>[CH2:1]([N:4]1[C:13](=[O:14])[C:12]2[N:11]([CH3:45])[C:10](/[CH:15]=[CH:16]/[C:17]3[N:18]=[CH:19][NH:20][CH:21]=3)=[N:9][C:8]=2[N:7]([CH2:41][CH2:42][CH3:43])[C:5]1=[O:6])[CH2:2][CH3:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 18915195HCID 18915195, compound

Product 1

HCID 178456462HCID 178456462, compoundYield 55%

Conditions

Temperature
50 °C

Procedure

The same procedure as in Example 2 was repeated using 1.96 g (3.44 mmol) of the mixture of Compound l and Compound m to give a crude product. The crude product was dissolved in 50 ml of methanol, and 1.5 ml of 1N hydrochloric acid was added to the solution, followed by stirring at 50° C. for 2 hours. After the solution was concentrated to about a half of its original volume, the concentrate was adjusted to pH 4 and extracted six times with chloroform. The organic layers were combined and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 10% methanol/chloroform) to give 640 mg (overall yield: 55%) of Compound 21 as an amorphous substance. The obtained Compound 21 (2.00 g) was treated with a hydrogen chloride/methanol solution and then recrystallized from isopropanol to give 1.04 g of hydrochloride of Compound 21.

Workup

  1. customto give a crude product
  2. concentrationAfter the solution was concentrated to about a half of its original volume
  3. extractionextracted six times with chloroform
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: 10% methanol/chloroform)

Sources & evidence

ORD record
ord-d15fd9f787dc47edb0330e4deb9a248d
Source dataset
uspto-grants-1998_05
Patent number
US05756735

Reaction notes

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