Trimethylsilyl iodide → HCID 86760980、化合物

HRID 1432953ノート

反応式

HRID 1432953 の反応式
[Si](I)(C)(C)C.C(OC([N:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]2[N:31]([S:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)(=[O:34])=[O:33])[C:30]3[CH:29]=[CH:28][N:27]=[C:26]([Cl:41])[C:25]=3[CH:24]=2)[C:18](=[O:42])[CH2:17]1)=O)C1C=CC=CC=1>CC#N>[C:35]1([S:32]([N:31]2[C:30]3[CH:29]=[CH:28][N:27]=[C:26]([Cl:41])[C:25]=3[CH:24]=[C:23]2[CH2:22][N:19]2[CH2:20][CH2:21][NH:16][CH2:17][C:18]2=[O:42])(=[O:33])=[O:34])[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

参加物

4

反応物 2

HCID 85247Trimethylsilyl iodideHCID 86760979HCID 86760979、化合物

生成物 1

HCID 86760980HCID 86760980、化合物収率 18.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

TMSI (2.7 mL, 19.0 mmol) is added to a solution of 4-(1-benzenesulfonyl-4-chloro-1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-3-oxo-piperazine-1-carboxylic acid benzyl ester (5.06 g, 9.38 mmol) in CH3CN (134 mL) at 0° C. The reaction mixture is warmed to RT and stirred for 5 hours. The reaction mixture is concentrated to dryness and the red residue is diluted with MeOH and concentrated to dryness (this is repeated twice). The mixture is diluted with CH2Cl2 and washed with saturated NaHCO3 and brine. The organic layer is dried over MgSO4, filtered and concentrated to dryness. The crude product is chromatographed eluting with 1-5% MeOH/CH2Cl2 to yield the title product (0.70 g, 1.74 mmol) and unreacted starting material (3.58 g, 6.64 mmol). 1H NMR (CDCl3, 300 MHz) δ8.20 (d, 1H), 7.93 (d, 1H), 7.85 (d, 2H), 7.60 (d, 1H), 7.51 (m, 2H), 6.50 (s, 1H), 5.01 (s, 2H), 3.45 (m, 2H), 3.18 (m, 2H). Ion spray [M+H]+=405, 407, Cl pattern.

後処理

  1. concentrationThe reaction mixture is concentrated to dryness
  2. additionthe red residue is diluted with MeOH
  3. concentrationconcentrated to dryness (this is repeated twice)
  4. additionThe mixture is diluted with CH2Cl2
  5. washwashed with saturated NaHCO3 and brine
  6. dry with materialThe organic layer is dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe crude product is chromatographed
  10. washeluting with 1-5% MeOH/CH2Cl2

出典と根拠

ORDレコード
ord-1aefe23132a6423eaf8495903b038abd
出典データセット
uspto-grants-2009_11
特許番号
US07612075B2

反応ノート

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