Pyrrolidine → HCID 69148506, compound

HRID 2218246Notes

Reaction equation

HRID 2218246 reaction equation
[NH2:1][C:2]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:7]=[C:6]([C:24]2[CH:29]=[CH:28][C:27](Cl)=[C:26]([N+:31]([O-:33])=[O:32])[CH:25]=2)[C:3]=1[C:4]#[N:5].[NH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1>CN(C=O)C>[NH2:1][C:2]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:7]=[C:6]([C:24]2[CH:29]=[CH:28][C:27]([N:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)=[C:26]([N+:31]([O-:33])=[O:32])[CH:25]=2)[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 69145732HCID 69145732, compound

Product 1

HCID 69148506HCID 69148506, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cold (0° C.) solution of 2-amino-6-(2-benzyloxyphenyl)-4-(4-chloro-3-nitrophenyl)nicotinonitrile (1.000 g, 2.189 mmol) in DMF (10 mL) was added pyrrolidine (0.778 g, 10.943 mmol). The mixture was stirred at room temperature for 2 hrs. and then at 60° C. for 2 hrs. The reaction mixture was partitioned between ethyl acetate and water. The separated organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was suspended in ethanol, and the precipitate was collected by filtration, washed with ethyl acetate and dried under reduced pressure to give 2-amino-6-(2-benzyloxyphenyl)-4-[3-nitro-4-(1-pyrrolidinyl)phenyl]nicotinonitrile as a yellow solid (0.990 g, yield 92%).

Workup

  1. waitand then at 60° C. for 2 hrs
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washThe separated organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. filtrationthe precipitate was collected by filtration
  8. washwashed with ethyl acetate
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-cff647e82b9d42bca3f6da2acc9510f5
Source dataset
uspto-grants-2008_08
Patent number
US07410986B2

Reaction notes

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