Ammonium Hydroxide → 3-[4-(5-Bromo-3-methylpyrid-2-yl)butyl]-6-(pyrid-3-ylmethyl)-3H-1,2,3-Triazolo[5,4-b]pyridine

HRID 1607035Notes

Reaction equation

N([O-])=O.[Na+].[NH2:5][C:6]1[C:7]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]2[C:29]([CH3:30])=[CH:28][C:27]([Br:31])=[CH:26][N:25]=2)=[N:8][CH:9]=[C:10]([CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:11]=1.[OH-].[NH4+:33]>O.S(=O)(=O)(O)O>[Br:31][C:27]1[CH:28]=[C:29]([CH3:30])[C:24]([CH2:23][CH2:22][CH2:21][CH2:20][N:19]2[C:7]3=[N:8][CH:9]=[C:10]([CH2:12][C:13]4[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=4)[CH:11]=[C:6]3[N:5]=[N:33]2)=[N:25][CH:26]=1

Participants

Conditions

Temperature: 4 °C

Procedure

Sodium nitrite (0.33 g) in water (20 ml) was added over 15 minutes to a solution of 3-amino-2-[4-(5-bromo-3-methylpyrid-2-yl)butylamino]-5-(pyrid-3-ylmethyl)pyridine (2.0 g) in molar sulphuric acid (100 ml) stirred at 4° C. The solution was then allowed to warm to room temperature, basified with concentrated ammonium hydroxide solution and extracted with chloroform (3 x 100 ml). The chloroform extracts were combined, dried over magnesium sulphate, and the solvent removed to give a product which was recrystallised from acetonitrile to give the title compound (1.49 g) as prims, m.p. 114°-115° C.

Workup

temperatureto warm to room temperature
extractionextracted with chloroform (3 x 100 ml)
dry with materialdried over magnesium sulphate
customthe solvent removed
customto give a product which
customwas recrystallised from acetonitrile

Sources & evidence

ORD record: ord-b5a54979e8fa435f860b60013c75f0bd
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04863933

Reaction notes

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