Benzaldehyde → 7-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-2-phenyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine

HRID 916651ノート

反応式

HRID 916651 の反応式
[F:1][C:2]1[C:3]([C:8]2[N:9]([CH2:13][C:14]3[N:19]=[CH:18][N:17]=[C:16]([NH:20][NH2:21])[C:15]=3[CH2:22][CH2:23][CH3:24])[CH:10]=[CH:11][N:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.C(=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.BrBr.[CH3:35]CO>>[F:1][C:2]1[C:3]([C:8]2[N:9]([CH2:13][C:14]3[N:19]=[CH:35][N:20]4[N:21]=[C:18]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[N:17]=[C:16]4[C:15]=3[CH2:22][CH2:23][CH3:24])[CH:10]=[CH:11][N:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 4

HCID 240BenzaldehydeHCID 702EthanolHCID 24408BromineHCID 57503304{6-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidin-4-yl}-hydrazine

生成物 1

HCID 113045167-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-2-phenyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine

実験手順

A mixture of {6-[2-(3,-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidin-4-yl}-hydrazine (131) (60 mg, 0.18 mmol), benzaldehyde (21 mg, 0.2 mmol) in EtOH is refluxed for 4 hours. Solvent is removed in vacuo. HOAc (2 mL) is added to the residue, and then bromine (0.3 mmol) is slowly added. The mixture is stirred at room temperature overnight. Solvent is removed in vacuo and the residue is treated with NaHCO3 (aq) and DCM. The organic layer is separated and the aqueous layer is extracted with DCM (2×0 mL). The combined organic layers are dried (MgSO4), the solvent is removed, and the crude purified by PTLC (10% MeOH in DCM) to give a white solid; 1H-NMR (CDCl3) δ: 8.93 (s, 1H), 8.44 (dd, 1H), 7.78–7.88 (m, 2H), 7.51–7.63 (m, 4H), 7.22–7.36 (m, 3H), 5.82 (s, 2H), 3.05 (q, 2H), 1.70–1.80 (m, 2H), 1.02 (t, 3H).

後処理

  1. temperatureis refluxed for 4 hours
  2. customSolvent is removed in vacuo
  3. additionHOAc (2 mL) is added to the residue
  4. customSolvent is removed in vacuo
  5. additionthe residue is treated with NaHCO3 (aq) and DCM
  6. customThe organic layer is separated
  7. extractionthe aqueous layer is extracted with DCM (2×0 mL)
  8. dry with materialThe combined organic layers are dried (MgSO4)
  9. customthe solvent is removed
  10. customthe crude purified by PTLC (10% MeOH in DCM)
  11. customto give a white solid

出典と根拠

ORDレコード
ord-ce530d4ec1374af4987022e6a833c09d
出典データセット
uspto-grants-2007_09
特許番号
US07271170B2

反応ノート

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