HCID 58406334, compound → HCID 86657084, compound

HRID 1753132Notes

Reaction equation

HRID 1753132 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]23[N:22]([C:23]([C:25]4[C:26]([CH3:30])=[N:27][O:28][CH:29]=4)=[O:24])[CH2:21][CH2:20][N:9]2[C:10](=[O:19])[C:11]2[N:12]([C:14]([CH2:17][OH:18])=[CH:15][CH:16]=2)[CH2:13]3)=[CH:4][CH:3]=1>C(Cl)Cl.O=[Mn]=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]23[N:22]([C:23]([C:25]4[C:26]([CH3:30])=[N:27][O:28][CH:29]=4)=[O:24])[CH2:21][CH2:20][N:9]2[C:10](=[O:19])[C:11]2[N:12]([C:14]([CH:17]=[O:18])=[CH:15][CH:16]=2)[CH2:13]3)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 58406334HCID 58406334, compound

Product 1

HCID 86657084HCID 86657084, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

10a-(4-chlorophenyl)-8-(hydroxymethyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (26 mg, 0.061 mmol) in CH2Cl2 (50 mL) was added MnO2 (26.5 mg, 0.30 mmol) and the reaction mixture was heated at 50° C. for 18 h. LCMS analysis after this time showed complete conversion of the starting material alcohol to the target aldehyde. The reaction mixture was filtered twice with a syringe filter and the filtrate was concentrated in vacuo to give 10a-(4-chlorophenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-5-oxo-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazine-8-carbaldehyde as a white solid (24 mg, yield 92%) The crude product was used in the next step without further purification. ESI-MI m/z [m+H]+ 425.1.

Workup

  1. filtrationThe reaction mixture was filtered twice with a syringe
  2. filtrationfilter
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-53a85d9e805d47378a02d9c06889b7a1
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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