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 73683노트

반응식

HRID 73683 반응식
[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

참가 물질

4

반응물 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 57955322HCID 57955322, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d9f766091ee84627b23327107c6f4a69
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829185B2

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