HCID 178448752, compound → HCID 178520821, compound

HRID 2242147Notes

Reaction equation

HRID 2242147 reaction equation
C([N:5]1[C:9]([NH:10][C:11](=[O:19])[CH2:12][CH2:13][N:14]2[CH:18]=[CH:17][CH:16]=[N:15]2)=[CH:8][C:7]([C@@H:20]2[CH2:23][C@H:22]([O:24][C:25](=[O:34])[NH:26][CH2:27][CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[CH2:21]2)=[N:6]1)(C)(C)C>C(O)(C(F)(F)F)=O>[N:14]1([CH2:13][CH2:12][C:11]([NH:10][C:9]2[NH:5][N:6]=[C:7]([C@@H:20]3[CH2:21][C@H:22]([O:24][C:25](=[O:34])[NH:26][CH2:27][CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)[CH2:23]3)[CH:8]=2)=[O:19])[CH:18]=[CH:17][CH:16]=[N:15]1

Participants

3

Reactant 1

HCID 178448752HCID 178448752, compound

Product 1

HCID 178520821HCID 178520821, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of cyclohexylmethyl-carbamic acid cis-3-[1-tert-butyl-5-(3-pyrazol-1-yl-propionylamino)-1H-pyrazol-3-yl]-cyclobutyl ester from Step A (122 mg) in TFA (2 mL) was heated at 120° C. in a microwave apparatus for 10 min. The solution was concentrated and the residue was dissolved in EtOAc. The resulting solution was washed sequentially with portions of saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography to afford the title product as a white solid. MS (M+H)+=415.5.

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThe resulting solution was washed sequentially with portions of saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-750775f380f14ffd8839029ab170e442
Source dataset
uspto-grants-2010_03
Patent number
US07671072B2

Reaction notes

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