Pyridine → HCID 66727106, compound

HRID 1845966Notes

Reaction equation

HRID 1845966 reaction equation
C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[C:12]([O:16][C:17]([N:19]1[CH2:25][CH2:24][CH2:23][N:22]([S:26]([C:29]2[CH:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[CH:35]=[N+:34]([O-])[CH:33]=[CH:32]3)(=[O:28])=[O:27])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[N:40]1C=CC=CC=1>>[NH2:40][C:35]1[C:36]2[C:31](=[CH:30][C:29]([S:26]([N:22]3[CH2:23][CH2:24][CH2:25][N:19]([C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])[CH2:20][CH2:21]3)(=[O:28])=[O:27])=[CH:38][CH:37]=2)[CH:32]=[CH:33][N:34]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 66726990HCID 66726990, compound

Product 1

HCID 66727106HCID 66727106, compound

Procedure

310 mg of p-toluenesulfonyl chloride was added to a pyridine (20 mL) solution of 510 mg of 6-(4-tert-butoxycarbonyl-1,4-diazepan-1-ylsulfonyl)isoquinoline 2-oxide obtained in Step 1 of Example 53, and the mixture was stirred at room temperature for 16 hours. Then, the reaction solvent was distilled off under reduced pressure. To the obtained residue, 9 mL of 2-ethanolamine was added, and the mixture was stirred at room temperature for 6 hours. After the completion of reaction, the reaction solution was poured into ice water, and the deposited white crystal was collected by filtration. The obtained crystal was purified by silica gel column chromatography (dichloromethane:methanol=30:1) to obtain 380 mg of the compound of interest as a white crystal (75%).

Workup

  1. distillationThen, the reaction solvent was distilled off under reduced pressure
  2. additionTo the obtained residue, 9 mL of 2-ethanolamine was added
  3. stirringthe mixture was stirred at room temperature for 6 hours
  4. customAfter the completion of reaction
  5. filtrationthe deposited white crystal was collected by filtration
  6. customThe obtained crystal was purified by silica gel column chromatography (dichloromethane:methanol=30:1)

Sources & evidence

ORD record
ord-34edab09fd5e43c0b3f2898d38f30729
Source dataset
uspto-grants-2015_02
Patent number
US08951997B2

Reaction notes

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