1-benzyl 4-tert-butyl ((1S)-1-[(5-amino-1-methyl-1H-pyrazol-4-yl)carbamoyl]tetramethylene}biscarbamate → HCID 86597892, compound

HRID 459640Notes

Reaction equation

HRID 459640 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[NH:8][C:9]([C@@H:11]([NH:23]C(=O)OCC1C=CC=CC=1)[CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:10]>CO.[Pd]>[NH2:23][C@H:11]([C:9]([NH:8][C:3]1[CH:4]=[N:5][N:6]([CH3:7])[C:2]=1[NH2:1])=[O:10])[CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:21])[CH3:19]

Participants

4

Reactant 1

HCID 865978881-benzyl 4-tert-butyl ((1S)-1-[(5-amino-1-methyl-1H-pyrazol-4-yl)carbamoyl]tetramethylene}biscarbamate

Product 1

HCID 86597892HCID 86597892, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of the crude product of 1-benzyl 4-tert-butyl {(1S)-1-[(5-amino-1-methyl-1H-pyrazol-4-yl)carbamoyl]tetramethylene}biscarbamate in methanol (200 ml) was treated with 10% palladium on carbon (1.0 g) under a hydrogen atmosphere at room temperature for 6 days. After the catalyst was filtered off, the filtrate was concentrated in vacuo. The residue was triturated with ether and dried in vacuo to give tert-butyl (4S)-4-amino-5-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-5-oxopentylcarbamate (5.5 g) as a solid.

Workup

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was triturated with ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-88bf97a529ea4e349e7d423b15ad5ac2
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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