154594-26-0 → HCID 22009915, compound

HRID 322068Notes

Reaction equation

HRID 322068 reaction equation
Cl.[N:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13]N)=[CH:9][CH:8]=2)[CH:6]=1.[Si]([O:22][CH:23]1[CH2:28][CH2:27][CH:26]([CH2:29][CH2:30][CH2:31][CH:32]=O)[CH2:25][CH2:24]1)(C(C)(C)C)(C)C>C(O)C.O.C(O)C>[N:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[C:11]3[C:10](=[CH:9][CH:8]=2)[NH:13][CH:32]=[C:31]3[CH2:30][CH2:29][CH:26]2[CH2:25][CH2:24][CH:23]([OH:22])[CH2:28][CH2:27]2)[CH:6]=1

Participants

5

Reactant 2

HCID 22009896154594-26-0HCID 22009912HCID 22009912, compound

Product 1

HCID 22009915HCID 22009915, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
140 °C

Procedure

A stirred mixture of 4-(1,2,4-triazol-4-yl)phenylhydrazine hydrochloride (930 mg, 3.5 mmol) in ethanol/water (25 ml, 4:1), under nitrogen, was slowly treated with a solution of 4-[4-(tert-butyldimethylsilanyloxy)cyclohexyl]butyraldehyde (1 g, 3.5 mmol) in ethanol (5 ml). The reaction mixture was heated at 140° C. for 18 hours in a sealed tube, cooled and evaporated. The residue was purified by column chromatography on silica using methanol/dichloromethane as eluent to afford the title compound as a mixture of cis and trans isomers (1 g, 92%). MS, ES+, m/z=311 for (M+H)+, δ(250 MHz, d6-DMSO) 1.07-1.88 (11H, m), 2.71 (2H, t, J=7 Hz), 3.70-3.78 (1H, m), 4.26 (1H, d, J=3 Hz), 7.21-7.32 (2H, m), 7.47 (1H, d, J=9Hz), 7.76 (1H, d, J=2Hz), 9.02 (2H, s), 11.10 (1H, br s).

Workup

  1. temperaturecooled
  2. customevaporated
  3. customThe residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-5f1ba95d1ec643a0ab14b52857bacca6
Source dataset
uspto-grants-2001_04
Patent number
US06211219B1

Reaction notes

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