Benzenesulfonyl chloride → HCID 66908232, compound

HRID 57158Notes

Reaction equation

HRID 57158 reaction equation
Cl.[S:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[NH2:11].[C:12]1([S:18]([Cl:21])(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>N1C=CC=CC=1>[ClH:21].[S:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[NH:11][S:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chloride2×HCID 66907303Thieno[3,2-b]pyridin-2-ylamine hydrochloride

Product 1

HCID 66908232HCID 66908232, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suspension of compound 146-A (0.65 g, 2.91 mmol) in pyridine (30 mL), at rt, was added benzenesulfonyl chloride (0.751 mL, 5.83 mmol), and the reaction was stirred for 16 h. Additional benzenesulfonyl chloride (0.225 mL, 1.76 mmol) was added and the reaction mixture was stirred at rt for an additional 16 h. The solvent was evaporated in vacuo, the residue treated with 1N HCl and extracted several times with dichloromethane and ethyl acetate. The aqueous layer was filtered, dissolved in methanol, and the combined organic extracts were evaporated in vacuo. The resultant residue was purified by reverse phase HPLC, eluting with an MeCN—H2O gradient to afford compound 146-B as an orange solid (0.24 g, 20%). 1H-NMR (CD3CN): δ 6.92 (s, 1H), 7.2 8.0 (d of d, 1H), 7.46 (m, 2H), 7.56 (m, 1H), 7.85 (m, 2H), 8.27 (d, 1H), 8.35 (d, 1H); MS: m/z 291.09 (MH+).

Workup

  1. stirringthe reaction mixture was stirred at rt for an additional 16 h
  2. customThe solvent was evaporated in vacuo
  3. additionthe residue treated with 1N HCl
  4. extractionextracted several times with dichloromethane and ethyl acetate
  5. filtrationThe aqueous layer was filtered
  6. dissolutiondissolved in methanol
  7. customthe combined organic extracts were evaporated in vacuo
  8. customThe resultant residue was purified by reverse phase HPLC
  9. washeluting with an MeCN—H2O gradient

Sources & evidence

ORD record
ord-8b5233d2c48c40f2b90229c4a4fffe68
Source dataset
uspto-grants-2016_09
Patent number
US09434711B2

Reaction notes

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