Water → HCID 178481900, compound

HRID 459618

Reaction equation

HRID 459618 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:31])[C@@H:10](NC(=O)OCC1C=CC=CC=1)[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C.FC(F)(F)S([N:44]=[C:45]([NH:54][C:55](=[O:61])[O:56][C:57]([CH3:60])([CH3:59])[CH3:58])[NH:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])(=O)=O.O>O1CCCC1.[Pd]>[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:31])[C@@H:10]([NH:44][C:45]([NH:54][C:55](=[O:61])[O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[N:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])[CH2:11][NH:12][C:13]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:19]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 36945701,3-Di-Boc-2-(trifluoromethylsulfonyl)guanidineHCID 865978712-benzyl 1-tert-butyl {(2S)-3-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-3-oxo-1,2-propanediyl}biscarbamate

Product 1

HCID 178481900HCID 178481900, compoundYield 77.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-benzyl 1-tert-butyl {(2S)-3-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-3-oxo-1,2-propanediyl}biscarbamate (1.58 g) in tetrahydrofuran (28 ml) was treated with 10% palladium on carbon (0.75 g) under a hydrogen atmosphere for 2 hours at room temperature. After the catalyst was filtered off, the filtrate was concentrated in vacuo to give a crude oil, which was dissolved in tetrahydrofuran (28 ml). To the solution were added triethylamine (2.04 ml) and di-tert-butyl ({[(trifluoromethyl)sulfonyl]imino}methylene)biscarbamate (2.86 g) successively at room temperature. The mixture was stirred at room temperature overnight. To the reaction mixture was added water to quench the reaction. The mixture was extracted with ethyl acetate. The organic layer was washed with water and brine. The extract was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to give di-tert-butyl {[((1S)-2-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-1-{[(tert-butoxycarbonyl)amino]methyl}-2-oxoethyl)amino]methylylidene}biscarbamate (1.53 g) as an amorphous solid.

Workup

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto give a crude oil, which
  4. customto quench
  5. customthe reaction
  6. extractionThe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water and brine
  8. dry with materialThe extract was dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f03c70a2ca544ebd8db8dd285dcf55f6
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Linked notes

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