HCID 131734430, compound → HCID 118373963, compound

HRID 588173Notes

Reaction equation

HRID 588173 reaction equation
C([O:8][C:9]1[C:13]2[CH:14]=[N:15][C:16]([NH:18][C:19]([NH:21][C@@H:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH3:23])=[O:20])=[CH:17][C:12]=2[N:11]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[N:10]=1)C1C=CC=CC=1.[H][H]>CCOC(C)=O.[Pd]>[O:8]=[C:9]1[C:13]2[CH:14]=[N:15][C:16]([NH:18][C:19]([NH:21][C@@H:22]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH3:23])=[O:20])=[CH:17][C:12]=2[N:11]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[NH:10]1

Participants

5

Reactant 2

HCID 131734430HCID 131734430, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 118373963HCID 118373963, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(R)-Ethyl 3-(benzyloxy)-6-(3-(1-phenylethyl)ureido)-1H-pyrazolo[4,3-c]pyridine-1-carboxylate (177.2 mg, 0.386 mmol) and Pd/C (4.10 mg, 0.039 mmol) were stirred in EtOAc (3.86 mL), under a balloon of hydrogen gas for 72 h. The reaction mixture was filtered through Celite, eluting with EtOAc. The filtrate was concentrated in vacuo to afford (R)-ethyl 3-oxo-6-(3-(1-phenylethyl)ureido)-2,3-dihydro-1H-pyrazolo[4,3-c]pyridine-1-carboxylate, which was carried onto the next step without further purification. MS ESI calc'd. For C18H19N5O4 [M+1]+370. found 370.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washeluting with EtOAc
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1909cc26891d454a826ec734f2186ec6
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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