Hydrochloric Acid → HCID 66993486, compound

HRID 518112Notes

Reaction equation

HRID 518112 reaction equation
C([N:8]1[CH2:14][C:13]2[N:15]=[CH:16][C:17]([N:19]3[CH:23]=[CH:22][N:21]=[C:20]3[CH3:24])=[N:18][C:12]=2[O:11][CH2:10][CH2:9]1)C1C=CC=CC=1.[ClH:25]>CO.[OH-].[OH-].[Pd+2]>[ClH:25].[CH3:24][C:20]1[N:19]([C:17]2[CH:16]=[N:15][C:13]3[CH2:14][NH:8][CH2:9][CH2:10][O:11][C:12]=3[N:18]=2)[CH:23]=[CH:22][N:21]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66993602HCID 66993602, compound

Product 1

HCID 66993486HCID 66993486, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 8-benzyl-3-(2-methyl-1H-imidazol-1-yl)-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepine (18 mg) in methanol (2.5 mL) was added 20% Pd(OH)2/C (10 mg), and the mixture was stirred under a hydrogen atmosphere at 50° C. for 5 hr. The reaction mixture was filtered, and the filtrate was concentrated. To a solution of the obtained crude product in methanol (0.3 mL) was added 0.1 N hydrochloric acid (410 μL), and the mixture was stirred for 30 min. The reaction mixture was concentrated, and the obtained crystals were purified by recrystallization (methanol-ethyl acetate) to give the title compound (6 mg, 61%) as a pale-yellow powder.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customTo a solution of the obtained crude product in methanol (0.3 mL)
  4. stirringthe mixture was stirred for 30 min
  5. concentrationThe reaction mixture was concentrated
  6. customthe obtained crystals were purified by recrystallization (methanol-ethyl acetate)

Sources & evidence

ORD record
ord-947220beefd54112aa54503145b416ad
Source dataset
uspto-grants-2015_08
Patent number
US09115139B2

Reaction notes

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