Triethylamine → HCID 58529715, compound

HRID 1972737Notes

Reaction equation

HRID 1972737 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11]3(O)[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11]3[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH:12]=3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 58529537HCID 58529537, compound

Product 1

HCID 58529715HCID 58529715, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of tert-butyl 4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-4-hydroxyazepane-1-carboxylate (2.45 g, 7.05 mmol) and triethylamine (2.95 mL, 21.2 mmol) in CH2Cl2 (49 mL) was added trifluoroacetic anhydride (1.99 mL, 14.1 mmol), dropwise. The ice bath was removed and the mixture was stirred at rt for 3 h. The reaction was quenched with H2O (40 mL) and the layers were separated. The organic phase was washed with brine, dried (Na2SO4), and concentrated to dryness. The crude residue was purified by ISCO® chromatography using 1:1 ethyl acetate/hexanes to afford 1.66 g (72%) of the desired product. ES-MS m/z 330.11 [M+H]+, HPLC RT (min) 2.47.

Workup

  1. customThe ice bath was removed
  2. customThe reaction was quenched with H2O (40 mL)
  3. customthe layers were separated
  4. washThe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to dryness
  7. customThe crude residue was purified by ISCO® chromatography

Sources & evidence

ORD record
ord-1ab3aa72aa0845eeab9d946de567a03f
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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