1,3-Dibromo-5,5-dimethylhydantoin → 4-(4-Amino-5-bromopyrrolo[2,1-f][1,2,4]triazin-7-yl)butan-1-ol

HRID 1972777노트

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HRID 1972777 반응식
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[N:6]2[N:5]=[CH:4][N:3]=1.[Br:16]N1C(C)(C)C(=O)N(Br)C1=O>O1CCCC1>[NH2:1][C:2]1[C:7]2=[C:8]([Br:16])[CH:9]=[C:10]([CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[N:6]2[N:5]=[CH:4][N:3]=1

참가 물질

4

반응물 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 585292824-(4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)butan-1-ol

생성물 1

HCID 585294014-(4-Amino-5-bromopyrrolo[2,1-f][1,2,4]triazin-7-yl)butan-1-ol수율 144.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-20 °C

실험 절차

To a cooled (−20° C.) solution of 4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)butan-1-ol (1.20 g, 5.82 mmol) in tetrahydrofuran (30 mL) was added 1,3-dibromo-5,5-dimethylhydantoin (832 mg, 2.91 mmol) in 4 portions over 10 min. The mixture was allowed to stir (−20° C.) for 3 h. The reaction was quenched with the addition saturated aqueous Na2SO3 (30 mL) and was allowed to warm to rt. The mixture was extracted with ethyl acetate (3×25 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated. The crude material was purified by ISCO® chromatography using a gradient of 75% to 100% ethyl acetate in hexanes to afford 1.2 g (72%) of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 7.81 (s, 1 H), 6.60 (s, 1 H), 4.37 (t, 1H), 3.39 (q, 2 H), 2.80 (t, 2 H), 1.70-1.60 (m, 2 H), 1.48-1.39 (m, 2 H); ES-MS m/z 285.1 [M+H]+, HPLC RT (min) 1.55.

후처리

  1. customThe reaction was quenched with the addition saturated aqueous Na2SO3 (30 mL)
  2. temperatureto warm to rt
  3. extractionThe mixture was extracted with ethyl acetate (3×25 mL)
  4. washThe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude material was purified by ISCO® chromatography

출처 및 근거

ORD 기록
ord-913a1cdbd0c247acaaf6bb864aab17a0
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431695B2

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