HCID 131734499, compound → HCID 118390792, compound

HRID 590873Notes

Reaction equation

HRID 590873 reaction equation
[C:1]([N:20]1[C:28]2[CH:27]=[C:26]([NH:29]C(=O)OC)[N:25]=[CH:24][C:23]=2[C:22]([NH:34][C:35](=[O:44])[O:36][CH2:37]C2C=CC=CC=2)=[N:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.CO.[Pd]>[NH2:29][C:26]1[N:25]=[CH:24][C:23]2[C:22]([NH:34][C:35](=[O:44])[O:36][CH3:37])=[N:21][N:20]([C:1]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:28]=2[CH:27]=1

Participants

5

Reactant 1

HCID 131734499HCID 131734499, compound

Product 1

HCID 118390792HCID 118390792, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 50 mL round bottom flask charged with benzyl methyl (1-trityl-1H-pyrazolo[4,3-c]pyridine-3,6-diyl)dicarbamate (126 mg, 0.216 mmol) in ethyl acetate (4 ml) and methanol (4 ml) was added palladium on carbon (45.9 mg, 0.043 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 (20 mL). The volatiles were removed in vacuo to afford crude methyl (6-amino-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate (95 mg, 0.211 mmol, 98% yield) as a white solid. MS ESI calc'd. For C27H24N5O2 [M+H]+ 450. found 450.

Workup

  1. customThe flask was evacuated
  2. additionback-filled with hydrogen gas
  3. filtrationThe palladium was filtered off
  4. washwashing through with ethyl acetate (20 mL)
  5. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-6e4282265da8482ca877bd49ba3c0d81
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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