Pyrrolidine → HCID 18381692, compound

HRID 2268892Notes

Reaction equation

HRID 2268892 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([CH2:14][C:15]2[C:20]([Cl:21])=[CH:19][N:18]=[CH:17][C:16]=2[Cl:22])=[N:4][N:3]=1.[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>CN(C=O)C>[Cl:22][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([Cl:21])[C:15]=1[CH2:14][C:5]1[C:6]2[C:11](=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)[C:2]([N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[N:3][N:4]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 186292104-Chloro-1-[(3,5-dichloropyridin-4-yl)methyl]-6-methoxyphthalazine

Product 1

HCID 18381692HCID 18381692, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-chloro-1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazine (1 g, 2.82 mmoles), prepared as described in example 45, in DMF (25 ml) was stirred under dry N2 at room temperature, and dropwise added with pyrrolidine. The mixture was heated at 100° C. for 20 hours, then concentrated and partitioned between water and CH2Cl2. The organic phase was washed with water, anhydrified and concentrated to give a solid which was crystallised from ethyl acetate (25 ml) to give 0.77 g of the title compound (yield: 71%). m.p.: 170-172° C.

Workup

  1. temperatureThe mixture was heated at 100° C. for 20 hours
  2. concentrationconcentrated
  3. custompartitioned between water and CH2Cl2
  4. washThe organic phase was washed with water, anhydrified
  5. concentrationconcentrated
  6. customto give a solid which
  7. customwas crystallised from ethyl acetate (25 ml)

Sources & evidence

ORD record
ord-d806606f04c8491eb959d7f17f0259e9
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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