4-(Chloromethyl)pyrimidine → 2-(Pyridazin-3-ylmethyl)isoindoline-1,3-dione

HRID 2067332Notes

Reaction equation

HRID 2067332 reaction equation
ClCC1C=CN=CN=1.Cl[CH2:10][C:11]1[N:12]=[N:13][CH:14]=[CH:15][CH:16]=1.[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.[K]>>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([CH2:10][N:21]2[C:17](=[O:27])[C:18]3[C:19](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:20]2=[O:22])[N:12]=1

Participants

4

Reactant 3

HCID 131235534-(Chloromethyl)pyrimidineHCID 142397123-(Chloromethyl)pyridazineHCID 24194345Phthalimide potassium salt

Product 1

HCID 666306162-(Pyridazin-3-ylmethyl)isoindoline-1,3-dioneYield 17%

Procedure

Following the procedure as described in step A of Preparation 14, making variations as required to replace 4-(chloromethyl)pyrimidine with 3-(chloromethyl)pyridazine (prepared according to R. W. Carling, et al., J. Med. Chem., (2004), Vol. 47, pp. 1807-1822) to react with potassium phthalimide, 2-(pyridazin-3-ylmethyl)isoindoline-1,3-dione was obtained as a colorless solid in 17% yield: 1H NMR (300 MHz, CDCl3) δ 9.12 (d, J=3.0 Hz, 1H), 7.90-7.85 (m, 2H), 7.78-7.72 (m, 2H), 7.51-7.43 (m, 2H), 5.21 (s, 2H); MS (ES+) m/z 240.1 (M+1).

Workup

  1. customas described in step A of Preparation 14
  2. customprepared

Sources & evidence

ORD record
ord-6b7b6d46df0e40e29c22cb42fdc9e40f
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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