Trifluoroacetic acid → N-(4-(((4-aminonaphthalen-1-yl)oxy)methyl)pyridin-2-yl)-6-ethylpyrazin-2-amine

HRID 63361노트

반응식

HRID 63361 반응식
C(O)(C(F)(F)F)=O.[CH2:8]([C:10]1[N:15]=[C:14]([NH:16][C:17]2[CH:22]=[C:21]([CH2:23][O:24][C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:28]([NH:35]C(=O)OC(C)(C)C)=[CH:27][CH:26]=3)[CH:20]=[CH:19][N:18]=2)[CH:13]=[N:12][CH:11]=1)[CH3:9]>C(Cl)Cl>[NH2:35][C:28]1[C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:25]([O:24][CH2:23][C:21]2[CH:20]=[CH:19][N:18]=[C:17]([NH:16][C:14]3[CH:13]=[N:12][CH:11]=[C:10]([CH2:8][CH3:9])[N:15]=3)[CH:22]=2)=[CH:26][CH:27]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 118317293Tert-butyl (4-((2-((6-ethylpyrazin-2-yl)amino)pyridin-4-yl)methoxy)naphthalen-1-yl)carbamate2회

생성물 1

HCID 118305959N-(4-(((4-aminonaphthalen-1-yl)oxy)methyl)pyridin-2-yl)-6-ethylpyrazin-2-amine수율 70.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

TFA (1.485 mL, 19.09 mmol) was added to a solution of tert-butyl (4-((2-((6-ethylpyrazin-2-yl)amino)pyridin-4-yl)methoxy)naphthalen-1-yl)carbamate (Intermediate D (protected)) (360 mg, 0.763 mmol) in DCM (15 mL), and the reaction mixture stirred at room temperature for 4 h, then concentrated in vacuo. The residue was combined with sat. sodium hydrogencarbonate solution and stirred at room temperature for 16 h. The solid was filtered, washing with acetonitrile, and dried under vacuum to give the subtitle compound N-(4-(((4-aminonaphthalen-1-yl)oxy)methyl)pyridin-2-yl)-6-ethylpyrazin-2-amine as a beige solid (200 mg, 69%); Rt 2.14 min (Method 2); m/z 372 (M+H)+ (ES+); 1H NMR δ: 1.20 (3H, t), 2.64 (2H, q), 5.18-5.24 (4H, overlapping m), 6.59 (1H, d), 6.82 (1H, d), 7.03 (1H, d), 7.41-7.51 (2H, overlapping m), 7.98-8.01 (2H, m), 8.04 (1H, m), 8.22-8.29 (2H, overlapping m), 8.91 (1H, s), 10.04 (1H, s).

후처리

  1. concentrationconcentrated in vacuo
  2. stirringstirred at room temperature for 16 h
  3. filtrationThe solid was filtered
  4. washwashing with acetonitrile
  5. customdried under vacuum

출처 및 근거

ORD 기록
ord-291dceeaa8ca472d938abcb908bbdb3a
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447076B2

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