Hydrochloric Acid → HCID 86684770, compound

HRID 579165Notes

Reaction equation

HRID 579165 reaction equation
[CH:1]1([CH:7]2[CH2:12][NH:11][CH2:10][C:9](=[O:13])[N:8]2[C:14]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[S:16][C:15]=2[C:25]([OH:27])=[O:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:28][C:29]1[N:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1.[OH-].[Na+].Cl>CC#N.CCOC(C)=O>[Cl:28][C:29]1[N:34]=[CH:33][C:32]([S:35]([N:11]2[CH2:10][C:9](=[O:13])[N:8]([C:14]3[CH:18]=[C:17]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[S:16][C:15]=3[C:25]([OH:27])=[O:26])[C@H:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[CH2:12]2)(=[O:37])=[O:36])=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 27927922-Chloro-5-pyridinesulfonyl chlorideHCID 66684920HCID 66684920, compound

Product 1

HCID 86684770HCID 86684770, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(2-cyclohexyl-6-oxo-piperazin-1-yl)-5-phenyl-thiophene-2-carboxylic acid (0.80 g, 1.90 mmol, 1.0 equiv) in MeCN (20 mL) at room temperature, was added 6-chloro-pyridine-3-sulfonyl chloride (1.10 g, 5.20 mmol, 2.7 equiv) and followed by NaOH (6.94 mL, 1.5 N solution, 10.4 mmol, 5.5 equiv) dropwise. The mixture was stirred at room temperature for 10 minutes. The mixture was acidified with 3 N HCl (2.5 mL), and then diluted with EtOAc (50 mL). The mixture was washed water (25 mL), brine (25 mL), dried (over Na2SO4), filtered and concentrated to give crude product (1.0 g, 94%) as yellow-green solid. MS: 560 [M−H+].

Workup

  1. washThe mixture was washed water (25 mL), brine (25 mL)
  2. dry with materialdried (over Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3d85445ff5cf40f6bf8fa46a41ba974d
Source dataset
uspto-grants-2015_05
Patent number
US09040690B2

Reaction notes

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