Hydrochloric Acid → HCID 91758304, compound

HRID 632810Notes

Reaction equation

HRID 632810 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][N:6]([C:9]2[C:13]([NH:14][C:15]([C:17]3[N:18]=[C:19]([C:22]4[CH:27]=[CH:26][N:25]=[C:24]([N:28]([CH2:36][C:37]([F:40])([F:39])[F:38])C(=O)OC(C)(C)C)[CH:23]=4)[O:20][CH:21]=3)=[O:16])=[CH:12][N:11]([CH3:41])[N:10]=2)[C:5]1=[O:42].Cl>C(OCC)(=O)C.CO>[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][N:6]([C:9]2[C:13]([NH:14][C:15]([C:17]3[N:18]=[C:19]([C:22]4[CH:27]=[CH:26][N:25]=[C:24]([NH:28][CH2:36][C:37]([F:38])([F:40])[F:39])[CH:23]=4)[O:20][CH:21]=3)=[O:16])=[CH:12][N:11]([CH3:41])[N:10]=2)[C:5]1=[O:42]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131735464HCID 131735464, compound

Product 1

HCID 91758304HCID 91758304, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of tert-butyl (4-(4-((3-(3-(2-hydroxyethyl)-2-oxoimidazolidin-1-yl)-1-methyl-1H-pyrazol-4-yl)carbamoyl)-1,3-oxazol-2-yl)pyridin-2-yl)(2,2,2-trifluoroethyl)carbamate (1.00 g) and 3M hydrogen chloride in a mixed solvent (10 mL) of ethyl acetate/methanol (1:1) was stirred overnight at room temperature. The precipitate was collected by filtration, and the obtained solid was washed with ethyl acetate/methanol (9:1), and dried under reduced pressure. To the obtained solid were added 1N aqueous sodium hydroxide solution (2.39 ml) and water (4 ml), and the mixture was stirred at room temperature for 30 min, and then at 0° C. for 30 min. The precipitate was collected by filtration, washed with water, and dried under reduced pressure to give the title compound (531 mg).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washthe obtained solid was washed with ethyl acetate/methanol (9:1)
  3. customdried under reduced pressure
  4. additionTo the obtained solid were added 1N aqueous sodium hydroxide solution (2.39 ml) and water (4 ml)
  5. stirringthe mixture was stirred at room temperature for 30 min
  6. waitat 0° C. for 30 min
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with water
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-bc5f769c4e7c42c8ae3749bf06c69d28
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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