Trifluoroacetic acid → N5-(3-(4-Amino-6-methyl-1,3,5-triazin-2-YL)-5-methoxypyridin-2-YL)-2-chloropyridine-3,5-diamine

HRID 1622013ノート

反応式

HRID 1622013 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[C:10]([NH:17][C:18]3[CH:19]=[C:20]([NH:25]C(=O)OC(C)(C)C)[C:21]([Cl:24])=[N:22][CH:23]=3)=[N:11][CH:12]=[C:13]([O:15][CH3:16])[CH:14]=2)[N:3]=1.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[C:10]([NH:17][C:18]3[CH:19]=[C:20]([NH2:25])[C:21]([Cl:24])=[N:22][CH:23]=3)=[N:11][CH:12]=[C:13]([O:15][CH3:16])[CH:14]=2)[N:3]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86647088Tert-butyl 5-(3-(4-amino-6-methyl-1,3,5-triazin-2-YL)-5-methoxypyridin-2-ylamino)-2-chloropyridin-3-ylcarbamate

生成物 1

HCID 59548238N5-(3-(4-Amino-6-methyl-1,3,5-triazin-2-YL)-5-methoxypyridin-2-YL)-2-chloropyridine-3,5-diamine収率 82.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a 20 mL scintillation vial which contained tert-butyl 5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-methoxypyridin-2-ylamino)-2-chloropyridin-3-ylcarbamate (0.210 g, 0.458 mmol) in DCM (5 mL) was added trifluoroacetic acid (Aldrich) (0.170 mL, 2.288 mmol). The resulting mixture was capped and stirred at rt in closed system for 1 h. The reaction mixture was first neutralized with sat. NaHCO3 then extracted with CHCl3 (3×10 mL). The combined organic layers were dried over MgSO4 and concentrated. The crude product was purified using the column chromatography (40 g, 3% to 5% MeOH in DCM) to afford the desired product as a yellow solid (135 mg). MS (ESI pos. ion) m/z: 359.0. Calc'd exact mass for C15H15Cl N8O: 358.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.45 (s, 3H) 3.84 (s, 3H) 5.43 (s, 2H) 7.78 (br. s., 1H) 7.86 (br. s., 1H) 7.89 (d, J=2.35 Hz, 1H) 7.94 (d, J=2.15Hz, 1H) 8.16 (d, J=3.13 Hz, 1H) 8.40 (d, J=3.13 Hz, 1H) 11.75 (s, 1H).

後処理

  1. customThe resulting mixture was capped
  2. extractionthen extracted with CHCl3 (3×10 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified

出典と根拠

ORDレコード
ord-c539a9f30dfd48d98c866adc21fe71db
出典データセット
uspto-grants-2014_07
特許番号
US08772480B2

反応ノート

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