Hydrochloric Acid → 5-Chloro-N-{1-[3-hydroxy-2-(hydroxymethyl)propyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-1H-indole-2-carboxamide

HRID 1376147Notes

Reaction equation

HRID 1376147 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH:14][CH:15]1[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH2:25][CH:26]3[CH2:31][O:30]C(C)(C)[O:28][CH2:27]3)[C:16]1=[O:34])=[O:13])=[CH:6]2>C1COCC1>[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH:14][CH:15]1[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH2:25][CH:26]([CH2:27][OH:28])[CH2:31][OH:30])[C:16]1=[O:34])=[O:13])=[CH:6]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 102386835-Chloro-N-{1-[(2,2-dimethyl-1,3-dioxan-5-yl)methyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-1H-indole-2-carboxamide

Product 1

HCID 103101385-Chloro-N-{1-[3-hydroxy-2-(hydroxymethyl)propyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-1H-indole-2-carboxamideYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6M aqueous HCl (2.34 mL) was added to 5-chloro-N-{1-[(2,2-dimethyl-1,3-dioxan-5-yl)methyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-1H-indole-2-carboxamide (Example 37; 540 mg, 1.16 mmol) in THF (19 mL) and the reaction was stirred for 1 h. The reaction was quenched by addition of triethylamine (1.5 mL) and the reaction was diluted with water (20 mL) and EtOAc (40 mL). The organic layer was separated, dried (MgSO4), filtered and evaporated. The residue was triturated with hot Et2O (15 mL) and after cooling was filtered and dried to afford the title compound (421 mg, 85%) as white solid.

Workup

  1. customThe reaction was quenched by addition of triethylamine (1.5 mL)
  2. additionthe reaction was diluted with water (20 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 (15 mL)
  8. temperatureafter cooling
  9. filtrationwas filtered
  10. customdried

Sources & evidence

ORD record
ord-04f9d429acdd44628b0d0391643c3ac0
Source dataset
uspto-grants-2007_01
Patent number
US07169927B2

Reaction notes

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