Sodium Carbonate → 8-[4-(1,3-Dioxolan-2-yl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-amine

HRID 1678746Notes

Reaction equation

HRID 1678746 reaction equation
[N:1]#[C:2]Br.C(=O)([O-])[O-].[Na+].[Na+].[O:10]1[CH2:14][CH2:13][O:12][CH:11]1[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[N:26][C:27]=3[NH:37][NH2:38])[N:22]=2)=[CH:17][CH:16]=1>CCO>[O:12]1[CH2:13][CH2:14][O:10][CH:11]1[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:29][C:28]3[C:27]4=[N:37][N:38]=[C:2]([NH2:1])[N:26]4[CH:25]=[CH:24][C:23]=3[N:22]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10476Cyanogen BromideHCID 594729242-[4-(1,3-dioxolan-2-yl)phenyl]-5-hydrazinyl-3-phenyl-1,6-Naphthyridine

Product 1

HCID 594729268-[4-(1,3-Dioxolan-2-yl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To dry EtOH (1 mL) was added cyanogen bromide (0.104 mL, 0.52 mmol, 5M in MeCN) followed by sodium carbonate (96 mg, 0.91 mmol). [2-(4-[1,3]Dioxolan-2-yl-phenyl)-3-phenyl-[1,6]naphthyridin-5-yl]-hydrazine (3-4, 100 mg, 0.26 mmol) was added and the mixture was stirred for 3 h. The reaction mixture was concentrated in vacuo and the resulting solid was used without further purification. LRMS m/z (M+1) Calcd: 410.2. Found 410.1.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting solid was used without further purification

Sources & evidence

ORD record
ord-f542c0a8bba94481ac17d7f90cd37acb
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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