Trifluoroacetic acid → HCID 178507614, compound

HRID 1486572Notes

Reaction equation

HRID 1486572 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]=[C:13]([NH:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]([NH:23]C(=O)OC(C)(C)C)=[N:21][CH:22]=3)[NH:12][N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:23][C:20]1[N:21]=[CH:22][C:17]([CH2:16][NH:15][C:13]2[NH:12][N:11]=[C:10]([NH:9][C:4]3[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=3)[N:14]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178452735HCID 178452735, compound

Product 1

HCID 178507614HCID 178507614, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 5-((3-(3,5-dichlorophenylamino)-1H-1,2,4-triazol-5-ylamino)methyl)pyridin-2-ylcarbamate Compound 6 (50 mg, 111 μmol) in DCM (1 ml) was added TFA (1 ml) and the reaction was stirred for 1 hour. The reaction mixture was concentrated in vacuo and was partitioned between DCM (5 ml) and sat. NaHCO3 (3 ml). The layers were separated and the aqueous layer was extracted with DCM (3×5 ml). The combined organic solution was washed with brine (5 ml), dried over Na2SO4, filtered and concentrated to give a white solid as desired product (10.2 mg, 26% yield). MS +m/z: 350 (M+H)+

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customwas partitioned between DCM (5 ml) and sat. NaHCO3 (3 ml)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with DCM (3×5 ml)
  5. washThe combined organic solution was washed with brine (5 ml)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bfe4b5383eb84c078df07037d31f1788
Source dataset
uspto-grants-2016_08
Patent number
US09428469B2

Reaction notes

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