1,3-Cyclohexanedione → HCID 178470343, compound

HRID 1696626Notes

Reaction equation

HRID 1696626 reaction equation
Cl.[NH2:2][C:3]1[CH:7]=[CH:6][NH:5][C:4]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH3:13][C:14]1[CH:30]=[CH:29][C:17]2[NH:18][C:19]([S:21][C:22]3[O:26][C:25]([CH:27]=O)=[CH:24][CH:23]=3)=[N:20][C:16]=2[CH:15]=1.[C:31]1(=O)[CH2:36][CH2:35][CH2:34][C:33](=[O:37])[CH2:32]1.C(N(CC)C(C)C)(C)C>C(O)C>[CH2:11]([O:10][C:8]([C:4]1[NH:5][CH:6]=[C:7]2[CH:27]([C:25]3[O:26][C:22]([S:21][C:19]4[NH:18][C:17]5[CH:29]=[CH:30][C:14]([CH3:13])=[CH:15][C:16]=5[N:20]=4)=[CH:23][CH:24]=3)[C:32]3[C:33](=[O:37])[CH2:34][CH2:35][CH2:36][C:31]=3[NH:2][C:3]=12)=[O:9])[CH3:12]

Participants

6

Reactant 4

HCID 104341,3-CyclohexanedioneHCID 81531DiisopropylethylamineHCID 164270913-Amino-2-ethoxycarbonylpyrrole hydrochlorideHCID 178423499HCID 178423499, compound

Product 1

HCID 178470343HCID 178470343, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

774 μmol of 3-amino-2-ethoxycarbonylpyrrole hydrochloride, 774 μmol of 5-(5-Methyl-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde (obtained from step 1), 774 μmol of 1,3 cyclohexanedione and 400 μL of N,N-diisopropylethylamine in 3 mL of ethanol are poured into a flask suitable for microwave irradiation (Personal Chemistry model Emrys Optimizer instrument). The flask is locked then irradiation is performed at 100° C. during 700 seconds. After cooling down to 20° C., the reaction mixture is concentrated under reduced pressure. The residue is purified on silica gel (Analogix model Intelliflash 280 instrument, SiO2 75 g; Eluent EtOAc/cyclohexane; from 10/90 to 80/20. (v/v), rate: 25 mL/min). The fractions containing the expected compound are combined and concentrated under reduced pressure. The remaining oil is solubilized in 0.5 mL of dichloromethane (DCM) then crystallized by addition of small amounts of diisopropyloxide. 60 mg of solid were collected.

Workup

  1. customirradiation
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. customThe residue is purified on silica gel (Analogix model Intelliflash 280 instrument, SiO2 75 g; Eluent EtOAc/cyclohexane; from 10/90 to 80/20. (v/v), rate: 25 mL/min)
  4. additionThe fractions containing the expected compound
  5. concentrationconcentrated under reduced pressure
  6. customthen crystallized by addition of small amounts of diisopropyloxide
  7. custom60 mg of solid were collected

Sources & evidence

ORD record
ord-ff7d56ac37c84813a485abc935683836
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

Loading…