Trifluoroacetic acid → HCID 10510985, compound

HRID 1913369Notes

Reaction equation

HRID 1913369 reaction equation
[CH3:1][N:2]([CH2:10][C:11]#[C:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][NH:2][CH2:10][C:11]#[C:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11447978HCID 11447978, compound

Product 1

HCID 10510985HCID 10510985, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 49 (43 mg, 0.17 mmol) in CH2Cl2 (0.8 mL) at 0° C. was added TFA (1.5 mL, excess), the ice bath was removed and the resultant solution was stirred at ambient temperature for 1 h. The solvent and excess TFA were removed under a stream of argon and the residue was dissolved in HCl(aq) (1.0 M, 1 mL) and washed with CH2Cl2 (3×10 mL). To the aqueous fraction was added CH2Cl2 (8 mL) and water (8 mL) and the pH was adjusted to 10 with NaOH(aq) (10 N) while stirring. The organic fraction was collected and the aqueous layer was extracted with CH2Cl2 (2×10 mL). The combined organic fractions were dried (Na2SO4), filtered and the solvent was removed in vacuo. The crude material was chromatographed on silica gel (CH3OH/CHCl3, 10/90, Rf=0.16) to afford the title compound 50 (13 mg, 53% yield) as an orange oil: 1H NMR (CDCl3) δ 8.65 (m, 1H), 8.51 (m, 1H), 7.07 (m, 1H), 7.23 (m, 1H), 3.64 (br s, 2H), 2.50 (br s, 3H); LRMS (ESI) m/z calcd for C9H11N2 [M+H]+ 147. found 147; LRMS (ESI) m/z calcd for C8H6N [M−NH(CH3)]+ 116. found 116; HRMS (ESI) m/z calcd for C9H11N2 [M+H]+ 147.0922. found 147.0921; HPLC>98% (tR=7.25 min, 60 (A):40 (B): 0.02 (C); tR=2.91 min, 60 (A):40 (B): 0.07 (C)).

Workup

  1. customthe ice bath was removed
  2. customThe solvent and excess TFA were removed under a stream of argon
  3. dissolutionthe residue was dissolved in HCl(aq) (1.0 M, 1 mL)
  4. washwashed with CH2Cl2 (3×10 mL)
  5. additionTo the aqueous fraction was added CH2Cl2 (8 mL) and water (8 mL)
  6. stirringwhile stirring
  7. customThe organic fraction was collected
  8. extractionthe aqueous layer was extracted with CH2Cl2 (2×10 mL)
  9. dry with materialThe combined organic fractions were dried (Na2SO4)
  10. filtrationfiltered
  11. customthe solvent was removed in vacuo
  12. customThe crude material was chromatographed on silica gel (CH3OH/CHCl3, 10/90, Rf=0.16)

Sources & evidence

ORD record
ord-ada224247508496e969ff7a5b1bb28da
Source dataset
uspto-grants-2013_12
Patent number
US08609708B2

Reaction notes

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