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

HRID 1972777ノート

反応式

HRID 1972777 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-913a1cdbd0c247acaaf6bb864aab17a0
出典データセット
uspto-grants-2013_04
特許番号
US08431695B2

反応ノート

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