Hydrochloric Acid → HCID 10194504, compound

HRID 1376149Notes

Reaction equation

HRID 1376149 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][C@@H:26]3[CH2:30][O:29]C(C)(C)[O:27]3)[C:16]1=[O:33])=[O:13])=[CH:6]2.C([O-])(O)=O.[Na+]>>[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][C@@H:26]([OH:27])[CH2:30][OH:29])[C:16]1=[O:33])=[O:13])=[CH:6]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 58788458HCID 58788458, compound

Product 1

HCID 10194504HCID 10194504, compoundYield 99%

Procedure

6N HCl was added dropwise to a solution of 5-chloro-N-(1-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-1H-indole-2-carboxamide (Method 7, 500 mg, 1.1 mmol) and the reaction was stirred at ambient temperature for 2 hours. Saturated NaHCO3 solution was added cautiously until the reaction mixture was at pH 8, the mixture was extracted with EtOAc (2×20 mL), the combined organic phases dried (MgSO4) and the volatiles removed under reduced pressure to give the title compound (450 mg, 99%) as a yellow solid.

Workup

  1. extractionthe mixture was extracted with EtOAc (2×20 mL)
  2. dry with materialthe combined organic phases dried (MgSO4)
  3. customthe volatiles removed under reduced pressure

Sources & evidence

ORD record
ord-a2896afed8ef443a9eadaaa7bae56827
Source dataset
uspto-grants-2007_01
Patent number
US07169927B2

Reaction notes

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