Hydrochloric Acid → 2-chloro-N-(1-(2,3-dihydroxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6H-thieno(2,3-b)pyrrole-5-carboxamide

HRID 1247500Notes

Reaction equation

HRID 1247500 reaction equation
Cl.CC1(C)[O:7][CH:6]([CH2:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH:11]([NH:19][C:20]([C:22]3[NH:26][C:25]4[S:27][C:28]([Cl:30])=[CH:29][C:24]=4[CH:23]=3)=[O:21])[C:10]2=[O:31])[CH2:5][O:4]1>C1COCC1>[Cl:30][C:28]1[S:27][C:25]2[NH:26][C:22]([C:20]([NH:19][CH:11]3[CH2:12][C:13]4[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=4)[N:9]([CH2:8][CH:6]([OH:7])[CH2:5][OH:4])[C:10]3=[O:31])=[O:21])=[CH:23][C:24]=2[CH:29]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21906856N-[1-(2,2-Dimethyl-1,3-dioxolan-4-ylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide

Product 1

HCID 117428502-chloro-N-(1-(2,3-dihydroxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6H-thieno(2,3-b)pyrrole-5-carboxamideYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6M Aqueous HCl (1.47 mL) was added to N-{1-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide (Method 3; 340 mg, 7.45 mmol) in THF (14 mL) and the reaction was stirred for 4 h. The reaction was quenched by addition of triethylamine (1.5 mL) then diluted with water (30 mL) and EtOAc (40 mL). The organic layer was separated, dried (MgSO4), filtered and evaporated. The residue was triturated with hot Et2O (10 mL) and after cooling was filtered and dried to afford the title compound (260 mg, 83%) as white solid.

Workup

  1. customThe reaction was quenched by addition of triethylamine (1.5 mL)
  2. additionthen diluted with water (30 mL) and EtOAc (40 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was triturated with hot Et2O (10 mL)
  8. temperatureafter cooling
  9. filtrationwas filtered
  10. customdried

Sources & evidence

ORD record
ord-4752315f99734addae676afcf4ac13ed
Source dataset
uspto-grants-2006_10
Patent number
US07129249B2

Reaction notes

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