Hydrochloric Acid → HCID 58406413, compound

HRID 1910920Notes

Reaction equation

HRID 1910920 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]23[N:23]([C:24]([C:26]4[C:27]([CH3:31])=[N:28][O:29][CH:30]=4)=[O:25])[CH2:22][CH2:21][N:10]2[C:11](=[O:20])[C:12]2[N:13]([CH:15]=[C:16]([C:18]#[N:19])[CH:17]=2)[CH2:14]3)=[CH:5][CH:4]=1.Cl>CO.[Pd]>[NH2:19][CH2:18][C:16]1[CH:17]=[C:12]2[C:11](=[O:20])[N:10]3[CH2:21][CH2:22][N:23]([C:24]([C:26]4[C:27]([CH3:31])=[N:28][O:29][CH:30]=4)=[O:25])[C:9]3([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH2:14][N:13]2[CH:15]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67370849HCID 67370849, compound

Product 1

HCID 58406413HCID 58406413, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred suspension of 10a-(4-methoxyphenyl)-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-7-carbonitrile (89) (220 mg, 0.53 mmol) in methanol (22 mL) was added Pd/C and conc. HCl (1.1 mL). The reaction was placed under an atmosphere of hydrogen and stirred at room temperature. Analysis by tlc and LCMS indicated a new product was forming. The crude material was purified by preparative HPLC to give 7-(aminomethyl)-10a-(4-methoxyphenyl)-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; trifluoroacetate salt (147) as an oil (44 mg, 16%).

Workup

  1. customwas forming
  2. customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-4160bba1b6d74dcd83e638fb8c3fcf7d
Source dataset
uspto-grants-2013_12
Patent number
US08604034B2

Reaction notes

Loading…