Propanal → HCID 10424901、化合物

HRID 1611700ノート

反応式

HRID 1611700 の反応式
[CH3:1][CH:2]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([NH2:19])[CH:15]=[CH:14]2)[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5].C([BH3-])#N.[CH:23](=O)[CH2:24][CH3:25]>CO.C(Cl)CCl>[CH2:23]([NH:19][C:16]1[CH:15]=[CH:14][C:13]2[C:18](=[C:9]([O:8][CH:2]([CH3:1])[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5])[CH:10]=[CH:11][CH:12]=2)[N:17]=1)[CH2:24][CH3:25]

参加物

5

反応物 3

HCID 527PropanalHCID 498716Cyano-borohydrideHCID 10083869HCID 10083869、化合物

生成物 1

HCID 10424901HCID 10424901、化合物

試薬・触媒・溶媒 1

HCID 22134543HCID 22134543、化合物溶媒

実験手順

To a 4 mL scintillation vial was added a stir bar and the title compound from Example 16 (15.0 mg, 0.058 mmol). To this was added 0.42 mL of a 1:1 MeOH/ClCH2CH2Cl mixture followed by MP-cyanoborohydride resin (84 mg, 3.7 equiv Argonaut Technologies, Inc.) and 40 μL (10 equiv) of propionaldehyde. The reaction vessel was placed in an oil bath that had been preheated to 80° C. and the contents were allowed to stir overnight. Upon cooling to room temperature, the suspension was filtered and the filtrate was evaporated in vacuo. The crude material was purified by reverse phase HPLC to afford the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 8.06 (d, 1H), 7.30 (m, 1H), 7.17 (m, 2H), 6.90 (d, 1H), 4.54–4.81 (m, 1H), 3.38 (m, 2H), 2.38 (m, 1H), 1.80 (m, 1H), 1.50 (m, 2H), 1.39 (d, 3H), 1.03 (t, 3H), 0.96 (s, 9H); MS (DCI/NH3) m/z 301 [M+H]+.

後処理

  1. additionTo a 4 mL scintillation vial was added a stir bar
  2. customThe reaction vessel was placed in an oil bath
  3. customhad been preheated to 80° C.
  4. filtrationthe suspension was filtered
  5. customthe filtrate was evaporated in vacuo
  6. customThe crude material was purified by reverse phase HPLC

出典と根拠

ORDレコード
ord-f8d54dcd541b4b0ab9275e5aaf4b6249
出典データセット
uspto-grants-2006_01
特許番号
US06989392B2

反応ノート

読み込み中…