Hydrochloric Acid → HCID 89462193, compound

HRID 1525318Notes

Reaction equation

HRID 1525318 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([NH:11][C:12](=[O:14])[CH3:13])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[Na+].[I-:16].Cl>CC#N>[I:16][C:2]1[N:7]=[CH:6][C:5]([C:8]([NH:11][C:12](=[O:14])[CH3:13])([CH3:10])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 77231171N-(2-(6-chloropyridin-3-yl)propan-2-yl)acetamide2×

Product 1

HCID 89462193HCID 89462193, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-(2-(6-chloropyridin-3-yl)propan-2-yl)acetamide, 33-c, (25 g, 0.12 mol) in MeCN (400 ml) was added NaI (353 g, 2.35 mol) and concentrated HCl (48 ml, 0.59 mol). The reaction mixture was then refluxed for 60 hours. Product conversion was monitored by LC-MS. The reaction mixture was filtered and the cake was washed with MeCN. The filtrate was concentrated under vacuo and the residue was diluted with ethyl acetate, washed with saturated aqueous Na2S203 and brine, dried and concentrated to give the product, 33-d, as a white solid (22 g, 61%).

Workup

  1. temperatureThe reaction mixture was then refluxed for 60 hours
  2. filtrationThe reaction mixture was filtered
  3. washthe cake was washed with MeCN
  4. concentrationThe filtrate was concentrated under vacuo
  5. additionthe residue was diluted with ethyl acetate
  6. washwashed with saturated aqueous Na2S203 and brine
  7. customdried
  8. concentrationconcentrated
  9. customto give the product, 33-d

Sources & evidence

ORD record
ord-a85382c956dd4b1f9d634e2c91555b04
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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