6-Chloronicotinoyl Chloride → HCID 86605971, compound

HRID 851960Notes

Reaction equation

HRID 851960 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][N:3]=1.[CH3:11][C:12]1[C:17]([CH3:18])=[C:16]([O:19][CH2:20][CH2:21][CH3:22])[CH:15]=[CH:14][C:13]=1[C@@H:23]([N:25]1[CH2:30][C@@H:29]2[CH2:31][C@H:26]1[CH2:27][NH:28]2)[CH3:24]>C(Cl)Cl.C([O-])(O)=O.[Na+].[OH-].[Na+]>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([N:28]2[CH2:27][C@@H:26]3[CH2:31][C@H:29]2[CH2:30][N:25]3[C@H:23]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][CH3:22])=[C:17]([CH3:18])[C:12]=2[CH3:11])[CH3:24])=[O:7])=[CH:9][CH:10]=1

Participants

6

Reactant 2

HCID 27821656-Chloronicotinoyl ChlorideHCID 69451611HCID 69451611, compound

Product 1

HCID 86605971HCID 86605971, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 6-chloronicotinoyl chloride (151 mg, 0.86 mmol) in 2 mL CH2Cl2 is added to a mixture of (1S,4S)-2-((S)-1-(2,3-dimethyl-4-propoxyphenyl)ethyl)-2,5-diaza-bicyclo[2.2.1]heptane in 5 mL of CH2Cl2 and aqueous NaHCO3 (saturated solution, 3 mL). The mixture is stirred vigorously at room temperature for 1 h. The mixture is then diluted with 1N NaOH (5 mL) and extracted CH2Cl2 (2×25 mL). The combined extracts are dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material is purified by flash chromatography on silicagel, eluting with CHCl3-MeOH (40:1 to 20:1) to afford the title compound. LC/MS: 428 (M+1).

Workup

  1. extractionextracted CH2Cl2 (2×25 mL)
  2. dry with materialThe combined extracts are dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material is purified by flash chromatography on silicagel
  6. washeluting with CHCl3-MeOH (40:1 to 20:1)

Sources & evidence

ORD record
ord-6fc318fc6da2485e978e692895ba3bc4
Source dataset
uspto-grants-2007_08
Patent number
US07253168B2

Reaction notes

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