Potassium Carbonate → HCID 66862682, compound

HRID 253007Notes

Reaction equation

HRID 253007 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([C@H:9]1[CH2:14][O:13][CH2:12][CH2:11][N:10]1S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)[CH3:8].BrC1C=CC(S)=CC=1.[Br:35][C:36]1[CH:44]=[CH:43][C:39]([C:40](O)=[O:41])=[CH:38][CH:37]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[Br:35][C:36]1[CH:44]=[CH:43][C:39]([C:40]([N:10]2[CH2:11][CH2:12][O:13][CH2:14][C@@H:9]2[CH2:7][CH3:8])=[O:41])=[CH:38][CH:37]=1

Participants

9

Reactant 7

HCID 11430Potassium CarbonateHCID 114644-Bromobenzoic acidHCID 660494-BromothiophenolHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66861351HCID 66861351, compound

Product 1

HCID 66862682HCID 66862682, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Potassium carbonate (49.1 mg, 0.355 mmol) was added to a solution of 89 mg (0.296 mmol) of the title compound produced in step (iii) of Reference Example 9 in N,N-dimethylformamide (1.0 ml), and the mixture was stirred at room temperature for 5 min. 4-Bromobenzenethiol (56.0 mg, 0.296 mmol) was added thereto, and the mixture was stirred at room temperature for 5 hr. Thereafter, N,N-dimethylformamide (1.0 ml), 119.0 mg (0.592 mmol) of 4-bromobenzoic acid, 80.0 mg (0.592 mmol) of 1-hydroxybenzotriazole, and 119.0 mg (0.592 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were successively added thereto, and the mixture was stirred at room temperature for 4.5 hr. A saturated aqueous sodium hydrogencarbonate solution was added thereto to stop the reaction, followed by extraction with ethyl acetate. The extract was dried over anhydrous sodium sulfate and was then filtered. The filtrate was concentrated under the reduced pressure and was then purified by preparative thin layer chromatography (hexane:ethyl acetate=1:4) to give 64 mg (2 steps, yield 72%) of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 5 hr
  2. stirringthe mixture was stirred at room temperature for 4.5 hr
  3. customthe reaction
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. filtrationwas then filtered
  7. concentrationThe filtrate was concentrated under the reduced pressure
  8. customwas then purified by preparative thin layer chromatography (hexane:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-2d9fc3b66bd44134a3d2dec12d6c8e9b
Source dataset
uspto-grants-2011_01
Patent number
US07871982B2

Reaction notes

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