Chlorosuccinimide → HCID 53353201、化合物

HRID 1478925ノート

反応式

HRID 1478925 の反応式
[OH:1][CH2:2][C@:3]([C:6]1[CH:25]=[CH:24][C:9]([C:10]([NH:12][C:13]2[N:18]=[CH:17][C:16]3[CH:19]=[CH:20][N:21]([CH2:22][CH3:23])[C:15]=3[CH:14]=2)=[O:11])=[CH:8][CH:7]=1)([OH:5])[CH3:4].[Cl:26]N1C(=O)CCC1=O>CN(C=O)C>[Cl:26][C:19]1[C:16]2[CH:17]=[N:18][C:13]([NH:12][C:10](=[O:11])[C:9]3[CH:24]=[CH:25][C:6]([C@@:3]([OH:5])([CH3:4])[CH2:2][OH:1])=[CH:7][CH:8]=3)=[CH:14][C:15]=2[N:21]([CH2:22][CH3:23])[CH:20]=1

参加物

4

反応物 2

HCID 31398Chlorosuccinimide2 回HCID 71087863HCID 71087863、化合物

生成物 1

HCID 53353201HCID 53353201、化合物収率 23%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

In a 50 mL pear flask was added (S)-4-(1,2-dihydroxypropan-2-yl)-N-(1-ethyl-1H-pyrrolo[3,2-c]pyridin-6-yl)benzamide (92 mg, 0.27 mmol) in DMF (2 ml) to give a solution. At room temperature 1-chloropyrrolidine-2,5-dione (36 mg, 0.27 mmol) was added, and the mixture was heated to 60° C. for 4 hours, at which point the reaction seemed to have stalled. An additional 0.2 equivalence of 1-chloropyrrolidine-2,5-dione was added, and the mixture was heated to 60° C. for another hour. The mixture was then cooled, and partitioned between brine and EtOAc. The aqueous layer was further extracted with EtOAc, and the organic layers were combined, washed with brine, dried, filtered and concentrated in vacuo. The residue was then triturated with hot EtOAc, and the resulting precipitate was collected on a fritted-glass funnel. The collected solid was then recrystallized from EtOH to give the product (S)-N-(3-chloro-1-ethyl-1H-pyrrolo[3,2-c]pyridin-6-yl)-4-(1,2-dihydroxypropan-2-yl)benzamide (23 mg, 0.062 mmol, 22% yield) as a pink solid. 1H NMR (DMSO-d6) δ 10.68 (s, 1 H), 8.60 (s, 1 H), 8.37 (s, 1 H), 8.02 (s, 2 H), 7.69 (s, 1 H), 7.59 (s, 2 H), 5.05 (s, 1 H), 4.76 (t, J=5.8 Hz, 1 H), 4.19 (q, J=7.1 Hz, 2 H), 3.40-3.50 (m, 2 H), 1.34-1.45 (m, 6 H); m.p. 223.0-223.9° C.

後処理

  1. customto give a solution
  2. temperaturethe mixture was heated to 60° C. for another hour
  3. temperatureThe mixture was then cooled
  4. custompartitioned between brine and EtOAc
  5. extractionThe aqueous layer was further extracted with EtOAc
  6. washwashed with brine
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was then triturated with hot EtOAc
  11. customthe resulting precipitate was collected on a fritted-glass funnel
  12. customThe collected solid was then recrystallized from EtOH

出典と根拠

ORDレコード
ord-6d28178fb225450d8e36515d0134aa50
出典データセット
uspto-grants-2016_08
特許番号
US09403819B2

反応ノート

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