Heptane → 1,4-dichloro-6-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyridazine

HRID 42225

Reaction equation

Br[CH2:2][C:3]1[C:8]([CH2:9]Br)=[C:7]([Cl:11])[N:6]=[N:5][C:4]=1[Cl:12].[C:13](=[O:16])([O-])[O-].[Na+].[Na+].C[C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1.CCCCCCC>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:12][C:4]1[C:3]2[CH2:2][N:25]([CH2:24][C:23]3[CH:26]=[CH:27][C:20]([O:16][CH3:13])=[CH:21][CH:22]=3)[CH2:9][C:8]=2[C:7]([Cl:11])=[N:6][N:5]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of 4,5-bis(bromomethyl)-3,6-dichloropyridazine (800 mg, 2.39 mmol) in 40 mL anhydrous THF was added with sodium carbonate (507 mg, 4.78 mmol) and tetrabutylammonium iodide (88.3 mg, 0.24 mmol). The reaction mixture was added with 4-methylbenzylamine (0.31 mL, 2.39 mmol) in 20 mL THF dropwisely for 2 h. The reaction mixture was heated at 70° C. for 8 h and concentrated. The crude material was dissolved in DCM and washed with water and brine. The organic solution was dried over Na2SO4 and concentrated to afford a crude oil. The mixture was purified by flash chromatography on silica gel, eluting with 10-80% EtOAc:heptane to afford a off-white solid (300 mg, yield: 41%).

Workup

concentrationconcentrated
dissolutionThe crude material was dissolved in DCM
washwashed with water and brine
dry with materialThe organic solution was dried over Na2SO4
concentrationconcentrated
customto afford a crude oil
customThe mixture was purified by flash chromatography on silica gel
washeluting with 10-80% EtOAc

Sources & evidence

ORD record: ord-5a00fc92a557426b89643e8e79018b9c
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536168B2

Linked notes

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