Potassium Carbonate → HCID 66749081, compound

HRID 2402041Notes

Reaction equation

HRID 2402041 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)[S:10][C:11]=2/[CH:12]=[N:13]/[S:14]([N:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:4][CH:3]=1.C1(C)C=CC(S([CH2:37][N+:38]#[C-:39])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:20]3[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=3)[S:10][C:11]=2[C:12]2[N:13]([S:14]([N:17]([CH3:18])[CH3:19])(=[O:16])=[O:15])[CH:39]=[N:38][CH:37]=2)=[CH:26][CH:27]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 87133970HCID 87133970, compound

Product 1

HCID 66749081HCID 66749081, compoundYield 30.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of N′-{(1E)-[4-(4-chlorobenzyl)-2-pyridin-4-yl-1,3-thiazol-5-yl]methylene}-N,N-dimethylsulfamide (148 mg, 0.352 mmol), p-tolylsulfonylmethyl isocyanide (75.5 mg, 0.387 mmol) and potassium carbonate (146 mg, 1.05 mmol) in DME (2.50 mL) was heated at 78° C. for 2 hours. The reaction was diluted with DCM (10 mL) and water (5 mL). The layers were separated and the aqueous layer was extracted with DCM (5 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (methanol/DCM=0/100→15/85) to give 50 mg of 5-(4-(4-chlorobenzyl)-2-(pyridin-4-yl)thiazol-5-yl)-N,N-dimethyl-1H-imidazole-1-sulfonamide. LC/MS (FA) ES+ 460. (Some of the deprotected product, 4-(4-chlorobenzyl)-5-(1H-imidazol-5-yl)-2-(pyridin-4-yl)thiazole, was also obtained (19 mg). This material was combined with the material obtained in the following deprotection step.)

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with DCM (5 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (methanol/DCM=0/100→15/85)

Sources & evidence

ORD record
ord-063dd4f018b74c638fd8cdeeccd8fc9b
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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