1,3-Dibromo-5,5-dimethylhydantoin → 5-Bromo-6-chloro-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

HRID 1094877ノート

反応式

HRID 1094877 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[N:9]([C:10]=1[CH2:11][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[N:8]=[CH:7][N:6]=[C:5]2[NH2:18].[Br:19]N1C(C)(C)C(=O)N(Br)C1=O>CN(C=O)C>[Br:19][C:3]1[C:2]([Cl:1])=[C:10]([CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:9]2[C:4]=1[C:5]([NH2:18])=[N:6][CH:7]=[N:8]2

参加物

4

反応物 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 57955322HCID 57955322、化合物

生成物 1

HCID 579552265-Bromo-6-chloro-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine収率 114.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 6-chloro-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (0.9 g, 3.36 mmol) in DMF (5 mL) at −20° C. was added 1,3-dibromo-5,5-dimethylhydantoin (0.43 g, 1.51 mmol) portion wise over 30 min. The reaction mixture was stirred for 20 minutes at that temperature. TLC analysis indicated that there was complete conversion of starting material. The reaction was quenched with distilled water (30 mL) as the solution warmed to rt. CH2Cl2 (30 mL) was added to the reaction and the solution was transferred to a separatory funnel and the organic layer was isolated while the aqueous layer was back extracted with CH2Cl2 (4×20 mL). The combined organic layers were collected, dried (MgSO4), filtered, and concentrated to dryness. The crude material was washed with diethyl ether (10 mL). The white precipitate was collected and dried under vacuum to yield 0.6 g of the above compound (1.73 mmol, yield 51%). 1H-NMR (CD3OD-d4) δ 7.94 (s, 1H), 3.79 (s, 2H), 3.05 (t, J=4.8 Hz, 4H), 2.39 (t, J=4.8 Hz, 4H); MS [M+H]+=347.7; LCMS RT=1.21 min.

後処理

  1. customThe reaction was quenched with distilled water (30 mL) as the solution
  2. additionCH2Cl2 (30 mL) was added to the reaction
  3. customthe solution was transferred to a separatory funnel
  4. customthe organic layer was isolated while the aqueous layer
  5. extractionwas back extracted with CH2Cl2 (4×20 mL)
  6. customThe combined organic layers were collected
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. washThe crude material was washed with diethyl ether (10 mL)
  11. customThe white precipitate was collected
  12. customdried under vacuum

出典と根拠

ORDレコード
ord-0225d938c8a141d0b2de628cad3be4ff
出典データセット
uspto-grants-2012_03
特許番号
US08133995B2

反応ノート

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