O-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl)-hydroxylamine → 4-[1-(4-Trifluoromethoxyphenyl)-1H-imidazol-4-yl]-benzaldehyde O-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl)-oxime

HRID 1470823Notes

Reaction equation

HRID 1470823 reaction equation
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[C:13]([C:15]3[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=3)[N:12]=[CH:11]2)=[CH:6][CH:5]=1.[CH3:25][O:26][C@@H:27]1[C@H:32]([O:33][CH3:34])[C@@H:31]([O:35][CH3:36])[C@H:30]([CH3:37])[O:29][C@H:28]1[O:38][NH2:39]>CCO>[CH3:25][O:26][C@@H:27]1[C@H:32]([O:33][CH3:34])[C@@H:31]([O:35][CH3:36])[C@H:30]([CH3:37])[O:29][C@H:28]1[O:38][N:39]=[CH:19][C:18]1[CH:21]=[CH:22][C:15]([C:13]2[N:12]=[CH:11][N:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:23])([F:1])[F:24])=[CH:5][CH:6]=3)[CH:14]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 57824423O-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl)-hydroxylamineHCID 578245224-[1-(4-trifluoromethoxyphenyl)-1H-imidazol-4-yl]-benzaldehyde

Product 1

HCID 866333884-[1-(4-Trifluoromethoxyphenyl)-1H-imidazol-4-yl]-benzaldehyde O-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl)-oximeYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-[1-(4-trifluoromethoxyphenyl)-1H-imidazol-4-yl]-benzaldehyde (50 mg, 0.15 mmol) and O-(2S,3R,4R,5S,6S)-(3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl)-hydroxylamine (45 mg, 0.20 mmol) were combined in 5 mL of dry EtOH, and the solution heated at reflux under a N2 atmosphere for 12 h. The resulting solution was concentrated in vacuo and purified by chromatography (Biotage, 1:1:1 Hexanes/EtOAc/DCM) to furnish 35 mg (44%) of Compound 26 as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.15 (s, 1H), 7.90 (s, 1H), 7.85 (d, J=6 Hz, 2H), 7.68 (d, J=6 Hz, 2H), 7.60 (s, 1H), 7.68 (s, 1H), 7.50 (d, J=6 Hz, 2H), 7.38 (d, J=6 Hz, 2H), 3.77 (dd, J=3.2, 2.0 Hz, 1H), 3.68 (dd, J=9.6, 6.2 Hz, 1H), 3.59 (s, 3H), 3.56 (s, 3H), 3.55 (s, 3H), 3.51 (m, 1H), 3.21 (t, J=9.3 Hz, 1H), 1.33 (d, J=6.1 Hz, 3H); MS 536.1 (M+H); mp 178° C. Anal. Calcd. for C16H10F3N3O2: C, 59.01; H, 5.50; N, 7.65. Found: C, 58.86; H, 5.58; N, 7.63.

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux under a N2 atmosphere for 12 h
  3. concentrationThe resulting solution was concentrated in vacuo
  4. custompurified by chromatography (Biotage, 1:1:1 Hexanes/EtOAc/DCM)

Sources & evidence

ORD record
ord-e78aa784d90a416e97c9ea50f8024541
Source dataset
uspto-grants-2015_04
Patent number
US09006468B2

Reaction notes

Loading…