Dimethylformamide → HCID 86615277, compound

HRID 1445134Notes

Reaction equation

HRID 1445134 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([N:9]1[C:13]2=[C:14]([N:20]3[CH2:29][CH2:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21]3)[N:15]=[C:16]([C:18]#[N:19])[CH:17]=[C:12]2[CH:11]=[C:10]1[CH3:30])[CH:7]=[CH2:8].CN(C)[CH:33]=[O:34]>ClCCl>[CH2:6]([N:9]1[C:13]2=[C:14]([N:20]3[CH2:29][CH2:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21]3)[N:15]=[C:16]([C:18]#[N:19])[CH:17]=[C:12]2[C:11]([CH:33]=[O:34])=[C:10]1[CH3:30])[CH:7]=[CH2:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 67141232HCID 67141232, compound

Product 1

HCID 86615277HCID 86615277, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phosphorus oxychloride (425 μl, 4.56 mmol) was added at room temperature to a solution of 1-allyl-7-(3,4-dihydro-1H-isoquinolin-2-yl)-2-methyl-1H-pyrrolo[2,3-c]pyridin-5-carbonitrile (1 g, 3.04 mmol) prepared in Step 3 in a mixture of anhydrous dichloromethane (20 ml) and N,N-dimethylformamide (353 μl, 4.56 mmol). The reaction mixture was refluxed for 3 hours, cooled to room temperature, and then filtered. The resulting solid washed with water and 1M sodium acetate (30 ml) was added thereto. The reaction mixture was stirred for 1 hour at room temperature and then filtered. The resulting solid washed with water and then dried to give 350 mg of the titled compound as a white solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. filtrationfiltered
  3. washThe resulting solid washed with water and 1M sodium acetate (30 ml)
  4. additionwas added
  5. filtrationfiltered
  6. washThe resulting solid washed with water
  7. customdried

Sources & evidence

ORD record
ord-a6393bea06c64e1ca75e88a12da52389
Source dataset
uspto-grants-2010_02
Patent number
US07662832B2

Reaction notes

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