Phenylsilane → 5-Cyclohex-1-enyl-3-(4-[1,2,4]triazol-1-yl-cyclohexylamino)-thiophene-2-carboxylic acid methyl ester

HRID 2099679Notes

Reaction equation

HRID 2099679 reaction equation
[N:1]1([CH:6]2[CH2:11][CH2:10][C:9](=O)[CH2:8][CH2:7]2)[CH:5]=[N:4][CH:3]=[N:2]1.[CH3:13][O:14][C:15]([C:17]1[S:18][C:19]([C:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=2)=[CH:20][C:21]=1[NH2:22])=[O:16].C1([SiH3])C=CC=CC=1>C([Sn](Cl)(Cl)CCCC)CCC>[CH3:13][O:14][C:15]([C:17]1[S:18][C:19]([C:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=2)=[CH:20][C:21]=1[NH:22][CH:9]1[CH2:10][CH2:11][CH:6]([N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)[CH2:7][CH2:8]1)=[O:16]

Participants

5

Reactant 3

HCID 12752PhenylsilaneHCID 574240934-[1,2,4]Triazol-1-yl-cyclohexanoneHCID 577954015-Cyclohex-1-enyl-3-aminothiophene-2-carboxylic acid methyl ester

Product 1

HCID 577954275-Cyclohex-1-enyl-3-(4-[1,2,4]triazol-1-yl-cyclohexylamino)-thiophene-2-carboxylic acid methyl esterYield 92.6%

Reagents, catalysts & solvents 1

HCID 12688Dibutyltin dichlorideCatalyst

Procedure

A mixture of intermediate 1, 4-[1,2,4]triazol-1-yl-cyclohexanone (257 mg, 1.55 mmol) and 3-Amino-5-cyclohex-1-enyl-thiophene-2-carboxylic acid methyl ester (compound x, see Irina) (368 mg, 1.55 mmol) was treated by dibutyltin dichloride (24 mg, 0.078 mmol). The resulting mixture was stirred 5 min at room temperature and phenylsilane (210 μl, 1.70 mmol) was added. The reaction mixture was stirred at room temperature under nitrogen for 40 h. Solvent was removed and the crude was purified by silica gel column chromatography using a gradient from 50% EtOAc:hexanes to 100% EtOAc as eluent to give 5-cyclohex-1-enyl-3-(4-[1,2,4]triazol-1-yl-cyclohexylamino)-thiophene-2-carboxylic acid methyl ester (555 mg, 92%) as a yellow mixture of cis and trans isomers.

Workup

  1. stirringThe reaction mixture was stirred at room temperature under nitrogen for 40 h
  2. customSolvent was removed
  3. customthe crude was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-24d5ce1749444f3a98ac4eb4c9c4dd91
Source dataset
uspto-grants-2009_08
Patent number
US07569600B2

Reaction notes

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