HCID 131735462, compound → HCID 91758304, compound

HRID 632807Notes

Reaction equation

HRID 632807 reaction equation
C([O:8][CH2:9][CH2:10][N:11]1[CH2:15][CH2:14][N:13]([C:16]2[C:20]([NH:21][C:22]([C:24]3[N:25]=[C:26]([C:29]4[CH:34]=[CH:33][N:32]=[C:31]([N:35]([CH2:43][C:44]([F:47])([F:46])[F:45])C(=O)OC(C)(C)C)[CH:30]=4)[O:27][CH:28]=3)=[O:23])=[CH:19][N:18]([CH3:48])[N:17]=2)[C:12]1=[O:49])C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[OH:8][CH2:9][CH2:10][N:11]1[CH2:15][CH2:14][N:13]([C:16]2[C:20]([NH:21][C:22]([C:24]3[N:25]=[C:26]([C:29]4[CH:34]=[CH:33][N:32]=[C:31]([NH:35][CH2:43][C:44]([F:45])([F:47])[F:46])[CH:30]=4)[O:27][CH:28]=3)=[O:23])=[CH:19][N:18]([CH3:48])[N:17]=2)[C:12]1=[O:49]

Participants

3

Reactant 1

HCID 131735462HCID 131735462, compound

Product 1

HCID 91758304HCID 91758304, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl (4-(4-((3-(3-(2-(benzyloxy)ethyl)-2-oxoimidazolidin-1-yl)-1-methyl-1H-pyrazol-4-yl)carbamoyl)-1,3-oxazol-2-yl)pyridin-2-yl)(2,2,2-trifluoroethyl)carbamate (400 mg) in TFA (4.0 mL) was stirred at room temperature for 3 hr, and the reaction mixture was concentrated under reduced pressure. A solution of the obtained residue and 20% palladium hydroxide-carbon (80 mg) in acetic acid (10 mL) was stirred at room temperature for 5 hr under hydrogen atmosphere (3 atm). The reaction mixture was filtered through a membrane filter, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate) and then silica gel column chromatography (methanol/ethyl acetate). The obtained solid was washed with a mixed solvent of ethyl acetate/hexane (1:1), and dried under reduced pressure to give the title compound (100 mg).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. filtrationThe reaction mixture was filtered through a membrane
  3. filtrationfilter
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate)
  6. washThe obtained solid was washed with a mixed solvent of ethyl acetate/hexane (1:1)
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-3c0a79de689b40cd9276bc2fde1feafa
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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