Semicarbazide hydrochloride → HCID 68864498, compound

HRID 494153Notes

Reaction equation

HRID 494153 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]2[N:11]3[CH2:25][CH2:24][N:23]([CH3:26])[C:22](=[O:27])[C:12]3=[C:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]=2[C:8](=[O:28])[N:7]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[C:32]([Cl:37])[CH:31]=2)[N:6]=1)=[O:4].Cl.[NH2:39][NH:40][C:41]([NH2:43])=[O:42].C(N(C(C)C)CC)(C)C>C1COCC1>[CH2:15]([O:14][C:13]1[C:9]2[C:8](=[O:28])[N:7]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[C:32]([Cl:37])[CH:31]=3)[N:6]=[C:5]([C:3](=[O:4])[CH2:2][NH:39][NH:40][C:41]([NH2:43])=[O:42])[C:10]=2[N:11]2[CH2:25][CH2:24][N:23]([CH3:26])[C:22](=[O:27])[C:12]=12)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 11236Semicarbazide hydrochlorideHCID 81531DiisopropylethylamineHCID 86624802HCID 86624802, compound

Product 1

HCID 68864498HCID 68864498, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of crude 4-bromoacetyl-10-(benzyloxy)-2-(3-chloro-4-fluorobenzyl)-8-methyl-7,8-dihydropyrazino[1′,2′:1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione (1.25 g, 2.13 mmol) in anhydrous THF, semicarbazide hydrochloride (0.35 g, 3.14 mmol), and diisopropylethylamine (0.66 mL, 3.77 mmol) was heated in a sealed tube at 100° C. for 30 minutes. The reaction mixture was concentrated under vacuum. The residue was dissolved in DMSO and subject to reverse phase preparative HPLC purification. Collection and lyophilization of appropriate fraction provided the intermediate 2-{2-[10-(benzyloxy)-2-(3-chloro-4-fluorobenzyl)-8-methyl-1,9-dioxo-1,2,6,7,8,9-hexahydropyrazino[1′,2′:1,5]pyrrolo[2,3-d]pyridazin-4-yl]-2-oxoethyl}hydrazinecarboxamide as white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutionThe residue was dissolved in DMSO
  3. customphase preparative HPLC purification
  4. customCollection and lyophilization of appropriate fraction

Sources & evidence

ORD record
ord-db89dd42e80d45f08f51572de3056c47
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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