Triethylamine → N-[5-[(E)-N'-hydroxycarbamimidoyl]-2-pyridinyl]-3,5-bis(phenylmethoxy)benzamide

HRID 133703ノート

反応式

HRID 133703 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:23]=[C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:25]=1)[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][N:16]=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.[NH2:42][OH:43]>C(O)C>[CH2:27]([O:26][C:24]1[CH:23]=[C:11]([CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:25]=1)[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([NH:42][OH:43])=[NH:22])=[CH:17][N:16]=1)=[O:13])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 230729493,5-bis(benzyloxy)-N-(5-cyanopyridin-2-yl)benzamide

生成物 1

HCID 178513344N-[5-[(E)-N'-hydroxycarbamimidoyl]-2-pyridinyl]-3,5-bis(phenylmethoxy)benzamide

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 3,5-bis(benzyloxy)-N-(5-cyanopyridin-2-yl)benzamide (212 mg, 0.49 mmol), triethylamine (170 μL, 1.22 mmol) and hydroxylamine hydrochloride (85 mg, 1.22 mmol) in ethanol (5 mL) was heated at reflux overnight. The mixture was cooled and concentrated under reduced pressure. The residue was purified by MPLC on silica eluting with 5% methanol/DCM then 15% methanol/DCM. The title compound was obtained as a colourless solid (171 mg, 75%). 1H NMR δ (d6-DMSO): 5.19 (4H, s); 5.92 (2H, s), 6.87 (1H, s); 7.28-7.48 (12H, m); 8.06 (1H, dd); 8.17 (1H, d), 8.65 (1H, s); 9.68 (1H, s); 10.85 (1H, br s); m/z (LCMS; ESI+) 469 (MH+).

後処理

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by MPLC on silica eluting with 5% methanol/DCM

出典と根拠

ORDレコード
ord-4295d3a4847d4f66903b0640ed354262
出典データセット
uspto-grants-2008_06
特許番号
US07390908B2

反応ノート

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