Trifluoroacetic anhydride → tert-butyl 5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydropyridine-1(2H)-carboxylate

HRID 1972733Notes

Reaction equation

HRID 1972733 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11]3(O)[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>N1C=CC=CC=1>[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11]3[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:12]=3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 58529617Tert-butyl 3-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3-hydroxypiperidine-1-carboxylate

Product 1

HCID 58529940tert-butyl 5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydropyridine-1(2H)-carboxylateYield 79.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a cooled (0° C.) solution of tert-butyl 3-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3-hydroxypiperidine-1-carboxylate (2.77 g, 8.31 mmol) in pyridine (55 mL) was added trifluoroacetic anhydride (2.35 mL, 14.1 mmol), dropwise. The ice bath was removed and the mixture was stirred at rt for 17 h. The mixture was concentrated to dryness. The crude solid was triturated with 3:1 EtOAc/hexanes then with MeOH to afford 2.09 g (76%) of the desired product. ES-MS m/z 316.04 [M+H]+, HPLC RT (min) 2.50.

Workup

  1. customThe ice bath was removed
  2. concentrationThe mixture was concentrated to dryness
  3. customThe crude solid was triturated with 3:1 EtOAc/hexanes

Sources & evidence

ORD record
ord-fd552793e9584660b17ce833826882b1
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

Loading…