Sodium Carbonate → HCID 178510374, compound

HRID 2402098Notes

Reaction equation

HRID 2402098 reaction equation
Cl.[Cl:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][C:8]2[N:9]=[C:10]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[S:11][C:12]=2[C:13](=[NH:15])[NH2:14])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:31][C:32](=O)[CH2:33][N:34]1C(=O)C2C(=CC=CC=2)C1=O>CN(C=O)C.C(OCC)(=O)C.O>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C:8]2[N:9]=[C:10]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[S:11][C:12]=2[C:13]2[NH:14][CH:31]=[C:32]([CH2:33][NH2:34])[N:15]=2)=[CH:22][CH:23]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2220372-(3-bromo-2-oxopropyl)-2,3-dihydro-1H-isoindole-1,3-dioneHCID 66747935HCID 66747935, compound

Product 1

HCID 178510374HCID 178510374, compoundYield 40.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-(4-chlorobenzyl)-2-(pyridin-4-yl)thiazole-5-carboximidamide hydrochloride (112 mg, 0.306 mmol) in DMF (2.96 mL) was added sodium carbonate (162 mg, 1.53 mmol) and 2-(3-bromo-2-oxopropyl)isoindoline-1,3-dione (95.0 mg, 0.337 mmol) and the resulting mixture was heated at 100 degrees for 4 hours. The reaction was cooled and taken up in ethyl acetate (30 mL) and water (5 mL). The layers were separated and the organic layer was washed with water (3×5 mL). The organic layer was dried, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (MeOH/DCM=0/100→10/90) to give 47 mg (30% yield) of the title compound. LC/MS (FA) ES+ 512. 514. 1H NMR (300 MHz, DMSO-d6) δ: 12.67 (bs, 1H), 8.69-8.67 (m, 2H), 7.91-7.79 (m, 6H), 7.27-7.24 (m, 3H), 7.11-7.08 (m, 2H), 4.77 (s, 2H), 4.45 (s, 2H).

Workup

  1. temperaturethe resulting mixture was heated at 100 degrees for 4 hours
  2. temperatureThe reaction was cooled
  3. customThe layers were separated
  4. washthe organic layer was washed with water (3×5 mL)
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography (MeOH/DCM=0/100→10/90)

Sources & evidence

ORD record
ord-4ee9271095994bd3846742470cc3ac85
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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