Sodium Hydroxide → 5-Chloro-3-(thiazolo[4,5-c]pyridin-2-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyridine

HRID 876842Notes

Reaction equation

[N:1]([O-])=O.[Na+].[Cl:5][C:6]1[N:11]=[C:10]([NH:12][CH2:13][C:14]2[S:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][C:17]=3[N:22]=2)[C:9]([NH2:23])=[CH:8][CH:7]=1.[OH-].[Na+]>O.CC(O)=O>[Cl:5][C:6]1[N:11]=[C:10]2[N:12]([CH2:13][C:14]3[S:15][C:16]4[CH:21]=[CH:20][N:19]=[CH:18][C:17]=4[N:22]=3)[N:1]=[N:23][C:9]2=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of NaNO2 (42.5 mg, 0.62 mmol) in H2O (0.5 mL) was added dropwise to a solution of 6-chloro-N2-(thiazolo[4,5-c]pyridin-2-ylmethyl)pyridine-2,3-diamine (90 mg, 0.31 mmol) in AcOH (1 mL) and H2O (1 mL) at 0° C. The reaction solution was stirred at 0° C. for 1 h, then basified with 30% aqueous NaOH to pH ˜9. The resulting precipitate was collected by filtration to afford the title compound. MS (m/z): 303 (M+1)+.

Workup

filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record: ord-bd47dbec834a4106959735447bd15152
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987269B2

Reaction notes

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