Isopropylamine → 2,6-Dihydro-2-methyl-6-(1-naphthalenylmethyl)-4-(2-propyl)amino-1H-pyrrolo[3,4-d]pyridazin-1-one

HRID 1835153Notes

Reaction equation

[CH:1]([NH2:4])([CH3:3])[CH3:2].Cl[C:6]1[C:7]2[C:8](=[CH:14][N:15]([CH2:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][CH:19]=3)[CH:16]=2)[C:9](=[O:13])[N:10]([CH3:12])[N:11]=1>C(O)C>[CH3:12][N:10]1[C:9](=[O:13])[C:8]2=[CH:14][N:15]([CH2:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][CH:19]=3)[CH:16]=[C:7]2[C:6]([NH:4][CH:1]([CH3:3])[CH3:2])=[N:11]1

Participants

Conditions

Temperature: 200 °C

Procedure

Isopropylamine (1 ml) was added to a solution of 4-chloro-2,6-dihydro-2-methyl-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyridazine-1-one (0.095 g) in ethanol (4 ml) and the mixture was heated in a sealed tube at 200° C. for 3 days then at 250° C. for 24 hours. The mixture was evaporated and the residue was purified by column chromatography, eluting with ethyl acetate followed by recrystallisation from ethyl acetate/isohexane to give the title compound (0.013 g).

Workup

customThe mixture was evaporated
customthe residue was purified by column chromatography
washeluting with ethyl acetate
customfollowed by recrystallisation from ethyl acetate/isohexane

Sources & evidence

ORD record: ord-e4484745bf3d4f51b5bcc7c5a4fabdbc
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06770646B2

Reaction notes

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