Thionyl Chloride → 2-(4-Fluorobenzyl)-10-methoxy-4-(1-chloroethyl)-8-methyl-7,8-dihydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione

HRID 494131Notes

Reaction equation

HRID 494131 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]3[C:14]([O:23][CH3:24])=[C:15]4[C:20](=[O:21])[N:19]([CH3:22])[CH2:18][CH2:17][N:16]4[C:10]=3[C:9]([CH:25](O)[CH3:26])=[N:8]2)=[CH:4][CH:3]=1.S(Cl)([Cl:32])=O>>[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]3[C:14]([O:23][CH3:24])=[C:15]4[C:20](=[O:21])[N:19]([CH3:22])[CH2:18][CH2:17][N:16]4[C:10]=3[C:9]([CH:25]([Cl:32])[CH3:26])=[N:8]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 688652402-(4-Fluorobenzyl)-10-methoxy-4-(1-hydroxyethyl)-8-methyl-7,8-dihydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione

Product 1

HCID 688663392-(4-Fluorobenzyl)-10-methoxy-4-(1-chloroethyl)-8-methyl-7,8-dihydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione

Procedure

A solution of 2-(4-fluorobenzyl)-10-methoxy-4-(1-hydroxyethyl)-8-methyl-7,8-dihydropyrazino[1′,2′:1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione (0.12 g, 0.30 mmol) in thionyl chloride (3.3 mL) was stirred at room temperature for 3 hours. The reaction mixture was concentrated under vacuum. The residue was concentrated from a solution in benzene under vacuum and triturated with diethyl ether. The solid precipitated was filtered and vacuum dried to provide the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. concentrationThe residue was concentrated from a solution in benzene under vacuum
  3. customtriturated with diethyl ether
  4. customThe solid precipitated
  5. filtrationwas filtered
  6. customvacuum dried

Sources & evidence

ORD record
ord-bb1fc5961f52474da6ddb0b1097b1962
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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