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Water → N,N-dimethyl-1-(2-(3-((methylsulfonyl)methyl)phenyl)-4-morpholinopyrrolo[2,1-f][1,2,4]triazin-6-yl)methanamine

HRID 63798
ノート
印刷プレビュー

反応式

HRID 63798 の反応式
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[N:18]=[C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:16]3=[CH:25][C:26]([CH2:28][N:29]([CH3:31])[CH3:30])=[CH:27][N:15]3[N:14]=2)[CH:8]=1)(=O)=O.[CH3:32][S:33]([O-:35])=[O:34].[Na+].O>CN1CCCC1=O>[CH3:31][N:29]([CH3:30])[CH2:28][C:26]1[CH:25]=[C:16]2[N:15]([CH:27]=1)[N:14]=[C:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([CH2:6][S:33]([CH3:32])(=[O:35])=[O:34])[CH:8]=1)[N:18]=[C:17]2[N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 962WaterHCID 2733271Sodium methanesulfinateHCID 117988030HCID 117988030、化合物

生成物 1

HCID 72201093N,N-dimethyl-1-(2-(3-((methylsulfonyl)methyl)phenyl)-4-morpholinopyrrolo[2,1-f][1,2,4]triazin-6-yl)methanamine収率 28%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

Compound 19 (45 mg, 0.1 mmol) and sodium methylsulfinate (41 mg, 0.4 mmol) were dissolved in 2 mL N-methylpyrrolidone. The mixture was under microwave irradiation for 30 minutes at 120° C. with the power of 100 watts. After completion of the reaction, the reaction mixture was poured into water, extracted for three times with ethyl acetate, and extracted for three times with dichloromethane. The organic layers were combined and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure to a small volume. The crude product was purified by a preparative plate (dichloromethane:methanol=6:1) to obtain 12 mg of white solid (28.0%). m.p. 143-144° C. 1H NMR (300 MHz, CDCl3): δ 8.32 (d, J=5.2 Hz, 1H), 8.29 (s, 1H), 7.63 (d, J=1.2 Hz, 1H), 7.50 (d, J=5.2 Hz, 2H), 6.78 (d, J=1.2 Hz, 1H), 4.34 (s, 2H), 4.11 (t, J=4.4 Hz, 4H), 3.88 (t, J=4.4 Hz, 4H), 3.66 (s, 2H), 2.78 (s, 3H), 2.36 (s, 6H). MS (EI) m/e (%): 429 (M+, 12).

後処理

  1. customThe mixture was under microwave irradiation for 30 minutes at 120° C. with the power of 100 watts
  2. customAfter completion of the reaction
  3. extractionextracted for three times with ethyl acetate
  4. extractionextracted for three times with dichloromethane
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure to a small volume
  7. customThe crude product was purified by a preparative plate (dichloromethane:methanol=6:1)

出典と根拠

ORDレコード
ord-2366236a36d94abc91175c5debdc09b4
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09447101B2

反応ノート

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