Toluene → HCID 71271126, compound

HRID 1752492Notes

Reaction equation

HRID 1752492 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[CH:9][C:8]([C:12]#[C:13][CH2:14][O:15][Si](C(C)(C)C)(C)C)=[CH:7][N:6]=1)=[O:4].C(O)(C(F)(F)F)=O.C1(C)C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[CH:9][C:8]([C:12]#[C:13][CH2:14][OH:15])=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 71271189HCID 71271189, compound

Product 1

HCID 71271126HCID 71271126, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-amino-5-[3-(tert-butyl-dimethyl-silanyloxy)-prop-1-ynyl)-pyridine-2-carboxylic acid methyl ester (711 mg, 2.22 mmol) in DCM (6 ml) was added 10.2 ml TFA (133 mmol) at 0° C. and the mixture was stirred at room temperature for 17 h. To the mixture was added toluene (18 ml) and the solvents were evaporated. The residue was dissolved in EtOAc (66 ml) and washed with aq. 1M Na2CO3 solution, the aq. Phase was extracted back with EtOAc. The combined organic layers were washed with half-saturated aq. sodium chloride, dried with Na2SO4 and evaporated. The residue was purified by chromatography on silica gel (DCM to DCM/MeOH 94:6) to provide the title compound as an off-white solid.

Workup

  1. customthe solvents were evaporated
  2. dissolutionThe residue was dissolved in EtOAc (66 ml)
  3. washwashed with aq. 1M Na2CO3 solution
  4. extractionthe aq. Phase was extracted back with EtOAc
  5. washThe combined organic layers were washed with half-saturated aq. sodium chloride
  6. dry with materialdried with Na2SO4
  7. customevaporated
  8. customThe residue was purified by chromatography on silica gel (DCM to DCM/MeOH 94:6)

Sources & evidence

ORD record
ord-2720c526673e4cfca3a4914a9dd6f14c
Source dataset
uspto-grants-2015_10
Patent number
US09163011B2

Reaction notes

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