1,1-Dimethoxyethyl(dimethyl)amine → N'-[(6S)-2-(3-Chloro-4-fluorobenzyl)-10-methoxy-8-ethyl-6-methyl-1,9-dioxo-1,2,6,7,8,9-hexahydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazin-4-yl]-N,N-dimethylethanimidamide

HRID 494143Notes

Reaction equation

HRID 494143 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][CH3:12])[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.CO[C:33](OC)([N:35]([CH3:37])[CH3:36])[CH3:34]>CN(C=O)C>[Cl:30][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][C:26]=1[F:29])[CH2:22][N:4]1[C:5](=[O:21])[C:6]2[C:10]([O:11][CH3:12])=[C:9]3[C:13](=[O:20])[N:14]([CH2:18][CH3:19])[CH2:15][C@H:16]([CH3:17])[N:8]3[C:7]=2[C:2]([N:1]=[C:33]([N:35]([CH3:37])[CH3:36])[CH3:34])=[N:3]1

Participants

4

Reactant 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 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 68865133N'-[(6S)-2-(3-Chloro-4-fluorobenzyl)-10-methoxy-8-ethyl-6-methyl-1,9-dioxo-1,2,6,7,8,9-hexahydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazin-4-yl]-N,N-dimethylethanimidamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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 (0.20 g, 0.46 mmol; Example 120, step 3) and N,N-dimethylacetamide dimethyl acetal (0.37 mL, 2.51 mmol) in anhydrous DMF (50 mL) was stirred in an oil bath at 40° C. overnight. The reaction mixture was concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with a 0-5% methanol in chloroform gradient. Collection and concentration of appropriate fractions provided the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-20e06b25089c494fa34aa358c33081b6
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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