HCID 68866136, compound → HCID 68867735, compound

HRID 494135Notes

Reaction equation

HRID 494135 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:5][N:6]1[C:11](=[O:12])[C:10]2[C:13]([O:22][CH3:23])=[C:14]3[C:19](=[O:20])[N:18]([CH3:21])[CH2:17][CH2:16][N:15]3[C:9]=2[C:8]([CH:24]([C:30]#[N:31])[CH2:25][C:26](OC)=[O:27])=[N:7]1>[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:5][N:6]1[C:11](=[O:12])[C:10]2[C:13]([O:22][CH3:23])=[C:14]3[C:19](=[O:20])[N:18]([CH3:21])[CH2:17][CH2:16][N:15]3[C:9]=2[C:8]([CH:24]2[CH2:25][C:26](=[O:27])[NH:31][CH2:30]2)=[N:7]1

Participants

3

Reactant 1

HCID 68866136HCID 68866136, compound

Product 1

HCID 68867735HCID 68867735, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A mixture of methyl 3-[2-(3-chloro-4-fluorobenzyl)-10-methoxy-8-methyl-1,9-dioxo-1,2,6,7,8,9-hexahydropyrazino[1′,2′:1,5]pyrrolo[2,3-d]pyridazin-4-yl]-3-cyanopropanoate (0.12 g, 0.24 mmol) and Raney nickel (200 mg; washed successively with deionized water until neutral to pH paper and three times with absolute ethanol) in absolute ethanol (35 mL) was subjected to an atmosphere of hydrogen gas at 50 psi in a Parr hydrogenation vessel at room temperature for 48 hours. The product mixture was filtered through a pad of Celite. The filtrate was concentrated under vacuum. The residue was subjected to reverse phase preparative HPLC purification. Collection and lyophilization of appropriate fractions provide the title compound. ES MS M+1=474

Workup

  1. washwashed successively with deionized water until neutral
  2. filtrationThe product mixture was filtered through a pad of Celite
  3. concentrationThe filtrate was concentrated under vacuum
  4. customphase preparative HPLC purification
  5. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-f3e140fc31f44e758969e30946896b3f
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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