HCID 69980578, compound → HCID 67031542, compound

HRID 2249596Notes

Reaction equation

HRID 2249596 reaction equation
C(OC(=O)[NH:7][C:8]([CH3:24])([CH3:23])[CH2:9][CH2:10][N:11]1[C:15]([CH3:16])=[CH:14][C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:12]1)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:24][C:8]([NH2:7])([CH3:23])[CH2:9][CH2:10][N:11]1[C:15]([CH3:16])=[CH:14][C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:12]1

Participants

3

Reactant 1

HCID 69980578HCID 69980578, compound

Product 1

HCID 67031542HCID 67031542, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

[1,1-Dimethyl-3-(5-methyl-3-phenyl-pyrazol-1-yl)-propyl]-carbamic acid tert-butyl ester (540 mg) was treated with TFA/CH2Cl2 3:1 (20 ml) at 0° C. for 2 hours. The resulting mixture was concentrated in vacuo and the residue was diluted with ethyl acetate. The organic layer was washed with a mixture of brine/sat. Na2CO3 and brine, dried and evaporated to give a crude oil. This was purified by flash chromatography (5% to 40% gradient of MeOH in CH2Cl2, 0.5% NH4OH content) to give the title compound (349 mg) as a yellow gum.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. additionthe residue was diluted with ethyl acetate
  3. washThe organic layer was washed with a mixture of brine/
  4. dry with materialNa2CO3 and brine, dried
  5. customevaporated
  6. customto give a crude oil
  7. customThis was purified by flash chromatography (5% to 40% gradient of MeOH in CH2Cl2, 0.5% NH4OH content)

Sources & evidence

ORD record
ord-a13c61871a0d46ba8692df9c82cb9906
Source dataset
uspto-grants-2008_01
Patent number
US07314884B2

Reaction notes

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