ethyl(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylimidate dihydrochloride → (-)-8-(6,6-dimethyltetrahydropyran-2-yl)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridine

HRID 546719Notes

Reaction equation

HRID 546719 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[CH:6]=[C:7](/[CH:17]=[CH:18]/[C:19](=[NH:23])OCC)[CH:8]=[CH:9][C:10]=1[N:11]1[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]1.Cl.Cl[CH2:26][CH2:27][CH2:28][CH:29]([CH:34]1[CH2:39][CH2:38][CH2:37][C:36]([CH3:41])([CH3:40])[O:35]1)[C:30]([NH:32][NH2:33])=O>>[CH3:40][C:36]1([CH3:41])[O:35][CH:34]([CH:29]2[CH2:28][CH2:27][CH2:26][N:32]3[N:33]=[C:19](/[CH:18]=[CH:17]/[C:7]4[CH:8]=[CH:9][C:10]([N:11]5[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]5)=[C:5]([O:4][CH3:3])[CH:6]=4)[N:23]=[C:30]23)[CH2:39][CH2:38][CH2:37]1

Participants

3

Reactant 2

HCID 66838954ethyl(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylimidate dihydrochlorideHCID 668390465-Chloro-2-(6,6-dimethyltetrahydropyran-2-yl)-valeric acid hydrazide hydrochloride

Product 1

HCID 66838972(-)-8-(6,6-dimethyltetrahydropyran-2-yl)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridine

Procedure

5.2 mg of a diastereomer mixture, 8-(6,6-dimethyltetrahydropyran-2-yl)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridine, was obtained according to the method in Example 113 from ethyl (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylimidate dihydrochloride obtained in Example 1 (47 mg) and 5-chloro-2-(6,6-dimethyltetrahydropyran-2-yl)-valeric acid hydrazide hydrochloride (36 mg). The diastereomer mixture was separated by CHIRALPAK™ IA manufactured by Daicel Chemical Industries, Ltd. (2 cm×25 cm, mobile phase: 30% ethanol-hexane) to obtain the title optically active compound with a retention time of 13 minutes and positive optical rotation (0.75 mg), the title optically active compound with a retention time of 14 minutes and positive optical rotation (0.21 mg), the title optically active compound with a retention time of 16 minutes and negative optical rotation (0.13 mg) and the title optically active compound with a retention time of 24 minutes and negative optical rotation (0.54 mg).

Workup

  1. customThe diastereomer mixture was separated by CHIRALPAK™ IA
  2. custom(2 cm×25 cm, mobile phase: 30% ethanol-hexane) to obtain the title optically active compound with a retention time of 13 minutes and positive optical rotation (0.75 mg)

Sources & evidence

ORD record
ord-335d782e1da342b6b15ff6d093bafa19
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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