Hydrochloric Acid → HCID 178425602, compound

HRID 1955600Notes

Reaction equation

HRID 1955600 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[N:12]=[N:11][C:10]([CH2:13][N:14]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]([CH2:25][C:26]4[N:27]=[N:28][N:29](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[N:30]=4)[C:17](=[O:50])[CH:16]([NH:51][C:52]([NH:54][C:55]4[CH:56]=[C:57]([CH3:61])[CH:58]=[CH:59][CH:60]=4)=[O:53])[C:15]3=[O:62])=[N:9]2)C=CC=CC=1.Cl.O>CO>[NH:30]1[C:26]([CH2:25][N:18]2[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:14]([CH2:13][C:10]3[NH:9][N:8]=[N:12][N:11]=3)[C:15](=[O:62])[CH:16]([NH:51][C:52]([NH:54][C:55]3[CH:56]=[C:57]([CH3:61])[CH:58]=[CH:59][CH:60]=3)=[O:53])[C:17]2=[O:50])=[N:27][N:28]=[N:29]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 54502453HCID 54502453, compound

Product 1

HCID 178425602HCID 178425602, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Compound 8k (353 mg, 0.363 mmol) in methanol (20 ml) is added 10% HCl (5 ml) and the mixture is stirred for 15 hr at room temperature. After the addition of water (150 ml), the mixture is extracted with ethyl acetate. The organic layer is washed with water and extracted with 10% aqueous sodium carbonate. The aqueous layer is acidified with 10% HCl and extracted with ethyl acetate. The extract is washed with water, dried over sodium sulfate, and distilled under reduced pressure to remove the solvent. Crystallization from methanol/benzene gives Compound 81 (118 mg, 66.7%).

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe organic layer is washed with water
  3. extractionextracted with 10% aqueous sodium carbonate
  4. extractionextracted with ethyl acetate
  5. washThe extract is washed with water
  6. dry with materialdried over sodium sulfate
  7. distillationdistilled under reduced pressure
  8. customto remove the solvent
  9. customCrystallization from methanol/benzene

Sources & evidence

ORD record
ord-307e72b2a53f45328471a359273f7b19
Source dataset
uspto-grants-1998_07
Patent number
US05776929

Reaction notes

Loading…