Pyridine, hydrofluoride (1:1) → HCID 68864695, compound

HRID 494145Notes

Reaction equation

HRID 494145 reaction equation
N[C:2]1[C:7]2[N:8]3[CH:16]([CH3:17])[CH2:15][N:14]([CH2:18][CH3:19])[C:13](=[O:20])[C:9]3=[C:10]([O:11][CH3:12])[C:6]=2[C:5](=[O:21])[N:4]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[C:25]([Cl:30])[CH:24]=2)[N:3]=1.N([O-])=O.[Na+].N1C=CC=CC=1.[FH:41]>>[Cl:30][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][C:26]=1[F:29])[CH2:22][N:4]1[C:5](=[O:21])[C:6]2[C:10]([O:11][CH3:12])=[C:9]3[C:13](=[O:20])[N:14]([CH2:18][CH3:19])[CH2:15][CH:16]([CH3:17])[N:8]3[C:7]=2[C:2]([F:41])=[N:3]1

Participants

4

Reactant 3

HCID 64774Pyridine, hydrofluoride (1:1)HCID 23668193Sodium NitriteHCID 68865427HCID 68865427, compound

Product 1

HCID 68864695HCID 68864695, compound

Procedure

To a stirred, cold (0° C.) solution of 4-amino-2-(3-chloro-4-fluorobenzyl)-10-methoxy-8-ethyl-6-methyl-7,8-dihydropyrazino[1′,2′:1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione (0.55 g, 1.26 mmol) in hydrogen fluoride-pyridine (9.5 mL) in a polyethylene tube, solid sodium nitrite (96 mg, 1.38 mmol) was added in small portions over a period of 10 minutes. The reaction mixture was stirred at room temperature for 1 hour. The product mixture was added dropwise into an ice-cold saturated aqueous sodium bicarbonate solution. The resultant mixture was extracted with ethyl acetate. The combined organic extract was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to afford the title material.

Workup

  1. extractionThe resultant mixture was extracted with ethyl acetate
  2. extractionThe combined organic extract
  3. washwas washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-12f696c11a3d4a919c052b0a8851b81c
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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