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

HRID 1972733노트

반응식

HRID 1972733 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-fd552793e9584660b17ce833826882b1
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431695B2

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