Methanol → (6S)-4-Amino-2-(3-chloro-4-fluorobenzyl)-10-hydroxy-8-ethyl-6-methyl-7,8-dihydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione

HRID 494139Notes

Reaction equation

HRID 494139 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]3[C@@H:16]([CH3:17])[CH2:15][N:14]([CH2:18][CH3:19])[C:13](=[O:20])[C:9]3=[C:10]([O:11]C)[C:6]=2[C:5](=[O:21])[N:4]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[C:25]([Cl:30])[CH:24]=2)[N:3]=1.B(Br)(Br)Br.CO>ClCCl>[NH2:1][C:2]1[C:7]2[N:8]3[C@@H:16]([CH3:17])[CH2:15][N:14]([CH2:18][CH3:19])[C:13](=[O:20])[C:9]3=[C:10]([OH:11])[C:6]=2[C:5](=[O:21])[N:4]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[C:25]([Cl:30])[CH:24]=2)[N:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 68865350(6S)-4-Amino-2-(3-chloro-4-fluorobenzyl)-10-methoxy-8-ethyl-6-methyl-7,8-dihydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione

Product 1

HCID 57682593(6S)-4-Amino-2-(3-chloro-4-fluorobenzyl)-10-hydroxy-8-ethyl-6-methyl-7,8-dihydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (6S)-4-amino-2-(3-chloro-4-fluorobenzyl)-10-methoxy-8-ethyl-6-methyl-7,8-dihydropyrazino[1′,2′:1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione (62 mg, 0.14 mmol) in anhydrous dichloromethane (2 mL), a solution of boron tribromide in dichloromethane (0.43 mL, 0.43 mmol; 1 M) was added. After stirring at room temperature for 30 minutes, the reaction mixture was treated with anhydrous methanol, stirred for 30 minutes, and concentrated under vacuum. The procedure was repeated twice. The residue was subjected to purification on preparative reverse phase high pressure column chromatography. Collection and lyophilization of appropriate fractions provided the title compound.

Workup

  1. stirringstirred for 30 minutes
  2. concentrationconcentrated under vacuum
  3. customThe residue was subjected to purification on preparative reverse phase high pressure column chromatography
  4. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-e9913f9d790240da8e7e9a963336aec4
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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