HCID 118390791, compound → HCID 118390790, compound

HRID 590868Notes

Reaction equation

HRID 590868 reaction equation
[C:1]([O:5][C:6](=[O:49])[N:7]([C:10]1[C:14]2[CH:15]=[N:16][C:17]([NH:19]C(OCC3C=CC=CC=3)=O)=[CH:18][C:13]=2[N:12]([C:30]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:11]=1)[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.CO.[Pd]>[C:1]([O:5][C:6](=[O:49])[N:7]([C:10]1[C:14]2[CH:15]=[N:16][C:17]([NH2:19])=[CH:18][C:13]=2[N:12]([C:30]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:11]=1)[CH2:8][CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 1

HCID 118390791HCID 118390791, compound

Product 1

HCID 118390790HCID 118390790, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 50 mL round bottom flask charged with tert-butyl(6-(((benzyloxy)carbonyl)amino)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)(ethyl)carbamate (225 mg, 0.344 mmol) in ethyl acetate (5 ml) and methanol (5 ml) was added palladium on carbon (73.3 mg, 0.069 mmol). The flask was evacuated and back-filled with hydrogen gas using an attached balloon. This procedure was attempted a further two times. The reaction mixture was stirred under a hydrogen atmosphere at room temperature for 16 h. The palladium was filtered off by passing the reaction mixture through celite and washing through with ethyl acetate. The volatiles were removed in vacuo to afford crude tert-butyl(6-amino-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)(ethyl)carbamate (159 mg, 0.306 mmol, 89% yield) which was taken forward without purification. MS ESI calc'd. For C32H34N5O [M+H]+ 520. found 520.

Workup

  1. customThe flask was evacuated
  2. additionback-filled with hydrogen gas
  3. filtrationThe palladium was filtered off
  4. washwashing through with ethyl acetate
  5. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-eb749ebdfd4b4c69a27c74bc28215fda
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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