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

HRID 63361

反応式

HRID 63361 の反応式
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

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 118317293Tert-butyl (4-((2-((6-ethylpyrazin-2-yl)amino)pyridin-4-yl)methoxy)naphthalen-1-yl)carbamate2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-291dceeaa8ca472d938abcb908bbdb3a
出典データセット
uspto-grants-2016_09
特許番号
US09447076B2

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