Trifluoroacetic acid → HCID 9858168, compound

HRID 896283Notes

Reaction equation

HRID 896283 reaction equation
[OH:1][C:2]1[C:3]([C:12]([NH:14][CH2:15][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18](C(OC(C)(C)C)=O)[CH:17]=2)=[O:13])=[N:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.FC(F)(F)C(O)=O>C(Cl)Cl>[OH:1][C:2]1[C:3]([C:12]([NH:14][CH2:15][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)=[O:13])=[N:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10295498HCID 10295498, compound

Product 1

HCID 9858168HCID 9858168, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 3-({[(8-hydroxy-1,6-naphthyridin-7-yl)carbonyl]amino}methyl)-1H-indole-1-carboxylate from Example 10 (12.0 mg, 0.0029 mmol) in CH2Cl2 (1 ml) was treated with trifluroacetic acid (TFA) (1 ml) and resulting mixture was stirred at room temperature for 1 hr and then the solvent was evaporated in vacuo. The resulting material was dissolved in DMSO (1 ml) and aged for 24 hrs at room temperature. This solution was purified by preparative HPLC. (Gilson semi preparative HPLC system and a YMC Combiprep Pro Column (50×20 mm I.D., C18, S-5 um, 120A) eluting with 5-95% acetonitrile/water (0.1% TFA) at 15 min/min) to afford the title compound after lyophilization.

Workup

  1. customresulting mixture
  2. customthe solvent was evaporated in vacuo
  3. dissolutionThe resulting material was dissolved in DMSO (1 ml)
  4. waitaged for 24 hrs at room temperature
  5. customThis solution was purified by preparative HPLC
  6. wash(Gilson semi preparative HPLC system and a YMC Combiprep Pro Column (50×20 mm I.D., C18, S-5 um, 120A) eluting with 5-95% acetonitrile/water (0.1% TFA) at 15 min/min)

Sources & evidence

ORD record
ord-b28da87e1760465a914231a03a49f373
Source dataset
uspto-grants-2005_07
Patent number
US06919351B2

Reaction notes

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