Pyridine → HCID 178472333, compound

HRID 452531Notes

Reaction equation

HRID 452531 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14](N)[N:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].N1C=CC=CC=1.N([O-])=O.[Na+].[FH:29]>>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:29])[N:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 1049PyridineHCID 14917Hydrofluoric AcidHCID 23668193Sodium NitriteHCID 178472334HCID 178472334, compound

Product 1

HCID 178472333HCID 178472333, compound

Procedure

Batch 1: To a solution of trans-4-(6-amino-pyridin-2-yl)-cyclohexanecarboxylic acid ethyl ester (0.050 g, 0.20 mmol) in 70% hydrogen fluoride in pyridine (0.47 ml, 18 mmol) was added solid sodium nitrite (0.015 g, 0.22 mmol) at 0-5° C. The cooling bath was removed after 20 minutes and the reaction mixture was stirred for 30 minutes at room temperature. The reaction mixture was partitioned between an ice-water mixture (50 ml) and tert-butyl methyl ether (50 ml). The organic layer was collected. The aqueous layer was extracted with two 50-ml portions of tert-butyl methyl ether. The combined organic layers were washed with one 30-ml portion of 2M aqueous sodium hydroxide solution and one 30-ml portion of brine, dried over anhydrous sodium sulfate and concentrated to dryness to give the crude title compound (0.08 g).

Workup

  1. customThe cooling bath was removed after 20 minutes
  2. customThe reaction mixture was partitioned between an ice-water mixture (50 ml) and tert-butyl methyl ether (50 ml)
  3. customThe organic layer was collected
  4. extractionThe aqueous layer was extracted with two 50-ml portions of tert-butyl methyl ether
  5. washThe combined organic layers were washed with one 30-ml portion of 2M aqueous sodium hydroxide solution and one 30-ml portion of brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-1d8ea747fe5643bab930978bc1aca8b7
Source dataset
uspto-grants-2013_07
Patent number
US08492376B2

Reaction notes

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