Dimedone → HCID 178470356, compound

HRID 1696627Notes

Reaction equation

HRID 1696627 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.[CH3:31][C:32]1([CH3:40])[CH2:39][C:37](=O)[CH2:36][C:34](=[O:35])[CH2:33]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:36]3[C:34](=[O:35])[CH2:33][C:32]([CH3:40])([CH3:31])[CH2:39][C:37]=3[NH:2][C:3]=12)=[O:9])[CH3:12]

Participants

6

Reactant 4

HCID 31358DimedoneHCID 81531DiisopropylethylamineHCID 164270913-Amino-2-ethoxycarbonylpyrrole hydrochlorideHCID 178423499HCID 178423499, compound

Product 1

HCID 178470356HCID 178470356, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

387 μmol of 3-amino-2-ethoxycarbonylpyrrole hydrochloride, 387 μmol of 5-(5-Methyl-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde (obtained from example 108, step 1), 387 μmol of dimedone and 202 μL of N,N-diisopropylethylamine in 1.5 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 40 g; Eluent EtOAc/cyclohexane; from 30/70 to 75/25. (v/v), rate: 25 mL/min, during 70 minutes). 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. 62 mg of expected compound are collected as a solid.

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 40 g; Eluent EtOAc/cyclohexane; from 30/70 to 75/25. (v/v), rate: 25 mL/min, during 70 minutes)
  4. additionThe fractions containing the expected compound
  5. concentrationconcentrated under reduced pressure
  6. customthen crystallized by addition of small amounts of diisopropyloxide
  7. custom62 mg of expected compound are collected as a solid

Sources & evidence

ORD record
ord-f259282d607040e8a873523bca28725d
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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