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

HRID 916651노트

반응식

HRID 916651 반응식
[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

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ce530d4ec1374af4987022e6a833c09d
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07271170B2

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