Dimethylformamide → HCID 22710840, compound

HRID 352935Notes

Reaction equation

HRID 352935 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:14][CH3:15])=[CH:9][CH2:10][C:11](O)=O)=[CH:4][CH:3]=1.[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22](S(C1C=CC=CC=1)(=O)=O)[C:21]([S:35]([N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH:39]1CC(OC)=O)(=[O:37])=[O:36])=[CH:20]2.[OH:49]N1C2C=CC=CC=2N=N1.CN1C[CH2:64][O:63][CH2:62][CH2:61]1.Cl.C(N=C=NCCCN(C)C)C.CN(C)[CH:80]=[O:81]>C(Cl)Cl>[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([S:35]([N:38]1[CH2:39][CH2:40][N:41]([C:80]([CH:11]3[CH2:15][CH2:14][C:8]([C:5]4[CH:6]=[CH:7][N:2]=[CH:3][CH:4]=4)=[CH:9][CH2:10]3)=[O:81])[CH:42]([CH2:61][C:62]([O:63][CH3:64])=[O:49])[CH2:43]1)(=[O:37])=[O:36])=[CH:20]2

Participants

8

Reactant 6

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22711029HCID 22711029, compoundHCID 69879395HCID 69879395, compound

Product 1

HCID 22710840HCID 22710840, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a mixture of methylene chloride (30 mL) and N,N-dimethylformamide (30 mL) was dissolved 4-(pyridin-4-yl)-3-hexenic acid hydrochloride (480 mg). Under ice cooling, 1-[(5-chloro-1-phenylsulfonylindol-2-yl)sulfonyl]-2-(methoxycarbonylmethyl)piperazine (1.024 g), 1-hydroxybenzotriazole (405 mg), N-methylmorpholine (607 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (575 mg) were added to the resulting solution. After 10 minutes, the mixture was allowed to rise back to room temperature, followed by stirring. After 48 hours, the reaction was terminated and the solvent was distilled off under reduced pressure. Ethyl acetate was added to the residue. The resulting mixture was washed with a saturated aqueous solution of sodium bicarbonate and saturated saline, dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue was subjected to chromatography on a silica gel column (methylene chloride:methanol=20:1), whereby the title compound (680 mg, colorless oil) was obtained.

Workup

  1. customto rise back to room temperature
  2. waitAfter 48 hours
  3. customthe reaction was terminated
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionEthyl acetate was added to the residue
  6. washThe resulting mixture was washed with a saturated aqueous solution of sodium bicarbonate and saturated saline
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent
  10. customwas obtained

Sources & evidence

ORD record
ord-0e6240aab41c452e9dab36e70c38d629
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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