Water → HCID 57920381, compound

HRID 2405874Notes

Reaction equation

HRID 2405874 reaction equation
Cl.Cl.[S:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[CH:5]=[C:4]1[NH2:12].[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[S:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[CH:5]=[C:4]1[NH:12][S:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chloride2×HCID 516892Sodium BicarbonateHCID 66907004Thieno[2,3-b]pyridin-2-ylamine dihydrochloride

Product 1

HCID 57920381HCID 57920381, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 147-E (0.22 g, 1.00 mmol) in pyridine (5.0 mL) was stirred at rt for 30 min, to which was added benzenesulfonyl chloride (0.135 mL, 1.05 mmol) and the reaction mixture was stirred at rt for 4 h. Another portion of benzenesulfonyl chloride (0.030 mL, 0.235 mmol) was added and the reaction mixture stirred at rt for 72 h. Water and saturated sodium bicarbonate solution were added and the mixture was extracted with dichloromethane, dried over sodium sulfate and evaporated in vacuo to afford a residue. Flash column chromatography (SiO2) eluting with dichloromethane afforded compound 147-F as a yellow solid (0.24 g, 83%).

Workup

  1. stirringthe reaction mixture stirred at rt for 72 h
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customto afford a residue
  6. washFlash column chromatography (SiO2) eluting with dichloromethane afforded compound 147-F as a yellow solid (0.24 g, 83%)

Sources & evidence

ORD record
ord-2a828f6b5d1749ad9c2268369fc595bf
Source dataset
uspto-grants-2014_08
Patent number
US08809327B2

Reaction notes

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