1-Methoxy-2-propanol → N-{2-[2-(4-Fluoro-3-morpholin-4-yl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-N-methyl-methanesulfonamide

HRID 1262026ノート

反応式

HRID 1262026 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.CS([C:18]1[N:23]=[CH:22][C:21]2=[CH:24][CH:25]=[C:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N:33]([CH3:38])[S:34]([CH3:37])(=[O:36])=[O:35])[N:20]2[N:19]=1)=O.C(N(CC)C(C)C)(C)C.COCC(O)C>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:18]2[N:23]=[CH:22][C:21]3=[CH:24][CH:25]=[C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[N:33]([CH3:38])[S:34]([CH3:37])(=[O:36])=[O:35])[N:20]3[N:19]=2)=[CH:4][C:3]=1[N:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1

参加物

5

反応物 4

HCID 79001-Methoxy-2-propanolHCID 81531DiisopropylethylamineHCID 392396264-Fluoro-3-(morpholin-4-yl)anilineHCID 54577677N-[2-(2-M ethanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamide

生成物 1

HCID 66711832N-{2-[2-(4-Fluoro-3-morpholin-4-yl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-N-methyl-methanesulfonamide収率 37.7%

実験手順

4-Fluoro-3-morpholin-4-yl-phenylamine (50.0 mg, 0.255 mmol), N-[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamide (46.4 mg, 0.127 mmol) and N,N-Diisopropylethylamine (0.0666 mL, 0.382 mmol) were dissolved in 1-Methoxy-2-propanol (0.50 mL, 5.1 mmol). The reaction was irradiated at 300 watts, 200° C. for 20 minutes or until HPLC showed consumption of starting material. The reaction mixture was then reduced and the crude residue was isolated and purified by Gilson prep HPLC to afford 23.77 mg of N-{2-[2-(4-Fluoro-3-morpholin-4-yl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-N-methyl-methanesulfonamide as a lyophilized powder. (M+H)=497.1. 1H NMR (400 MHz, DMSO, d6) δ 9.36 (s, 1H), 8.97 (s, 1H), 7.72 (m, 1H), 7.67 (m, 1H), 7.54 (m, 3H), 6.96 (m, 3H), 6.87 (m, 1H), 3.59 (m, 4H), 3.07 (s, 3H), 2.79 (s, 3H), 2.55 (m, 4H).

後処理

  1. customThe reaction was irradiated at 300 watts, 200° C. for 20 minutes or until HPLC
  2. customconsumption of starting material
  3. customthe crude residue was isolated
  4. custompurified by Gilson prep HPLC

出典と根拠

ORDレコード
ord-98180dbedfb3467fa7a197a660bba034
出典データセット
uspto-grants-2013_06
特許番号
US08471005B2

反応ノート

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