Water → HCID 9913495, compound

HRID 1743405Notes

Reaction equation

HRID 1743405 reaction equation
I[CH2:2][C:3]1([CH3:19])[O:14][C:13]2[C:5](=[C:6]3[C:10](=[C:11]([CH3:16])[C:12]=2[CH3:15])[NH:9][C:8]([CH3:18])([CH3:17])[CH2:7]3)[CH2:4]1.Cl.[CH3:21][N:22]([CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)[C:23]1[S:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C(=O)C>[CH3:21][N:22]([CH:32]1[CH2:37][CH2:36][N:35]([CH2:2][C:3]2([CH3:19])[O:14][C:13]3[C:5](=[C:6]4[C:10](=[C:11]([CH3:16])[C:12]=3[CH3:15])[NH:9][C:8]([CH3:18])([CH3:17])[CH2:7]4)[CH2:4]2)[CH2:34][CH2:33]1)[C:23]1[S:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 9929328HCID 9929328, compoundHCID 69642317HCID 69642317, compound

Product 1

HCID 9913495HCID 9913495, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
180 °C

Procedure

A suspension of 1,6,7,8-tetrahydro-2-(iodomethyl)-2,4,5,7,7-pentamethyl-2H-furo[3,2-e]indole (372 mg, 1.0 mmol), N-methyl-N-(4-piperidinyl)-1,3-benzothiazole-2-amine hydrochloride (427 mg, 1.5 mmol) and potassium carbonate (485 mg, 3.5 mmol) in N,N-dimethylacetamide (2 mL) was stirred at 180° C. for 6 hours under the nitrogen atmosphere. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate two times. The combined organic layers were washed with water and saturated brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was subjected to basic silica gel column chromatography (hexane-ethyl acetate 10:1), and recrystallized from ethyl acetate-hexane to obtain 276 mg of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate two times
  2. washThe combined organic layers were washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-fb2ca5a8d2894dedb868c061c502ca56
Source dataset
uspto-grants-2006_03
Patent number
US07008940B1

Reaction notes

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