Hydrochloric Acid → HCID 18449220, compound

HRID 1270174Notes

Reaction equation

HRID 1270174 reaction equation
[CH:1]([O:4][CH2:5][CH2:6][NH:7][C:8]([C:10]1[CH:19]=[C:18]2[C:13]([N:14]=[C:15]([NH:24][CH:25]([CH3:27])[CH3:26])[C:16]3[N:17]2[C:20](=[O:23])[NH:21][N:22]=3)=[CH:12][CH:11]=1)=O)([CH3:3])[CH3:2].[BH4-].[Na+].B(F)(F)F.CCOCC.Cl>C1COCC1.C(Cl)Cl.[OH-].[Na+]>[CH:1]([O:4][CH2:5][CH2:6][NH:7][CH2:8][C:10]1[CH:19]=[C:18]2[C:13]([N:14]=[C:15]([NH:24][CH:25]([CH3:27])[CH3:26])[C:16]3[N:17]2[C:20](=[O:23])[NH:21][N:22]=3)=[CH:12][CH:11]=1)([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 18449193HCID 18449193, compound

Product 1

HCID 18449220HCID 18449220, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
23 °C

Procedure

A suspension of 30 mg of 4-isopropylamino-1-oxo-1,2-dihydro-[1,2,4]triazolo[4,3-a]quinoxaline-8-carboxylic acid-(2-isopropoxy-ethyl)-amide in THF (5.0 mL) was stirred as sodium borohydride (30 mg) was added. This mixture was heated to reflux and then boron trifluoride etherate (0.15 mL) was added dropwise. The mixture was refluxed for two hr. and then cooled to 23° C. and acidified to pH 3.0 with 3N HCl. After stirring for 30 min., the reaction was diluted with methylene chloride and basified to pH 14 with 6N sodium hydroxide. The layers were separated and the aqueous was extracted with methylene chloride and the combined organic layers were dried over sodium sulfate, filtered, and concentrated. Purification of the residue by silica gel chromatography provided the product as a white solid. MS (M+H)+=359.0.

Workup

  1. additionwas added
  2. temperatureThis mixture was heated
  3. temperatureto reflux
  4. temperatureThe mixture was refluxed for two hr
  5. customThe layers were separated
  6. extractionthe aqueous was extracted with methylene chloride
  7. dry with materialthe combined organic layers were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification of the residue by silica gel chromatography

Sources & evidence

ORD record
ord-a2f0b920414246728d921101200afe0e
Source dataset
uspto-grants-2007_04
Patent number
US07202245B2

Reaction notes

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