Acetic Acid → N-(5-Chloro-3-(quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyridin-7-yl)acetamide

HRID 876849Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

N-(3-amino-6-chloro-2-(quinolin-6-ylmethylamino)pyridin-4-yl)acetamide was added to a solution of acetic acid (2 mL) and water (2 mL) at 0° C., followed by the addition of NaNO2 (180 mg, 2.6 mmol) in H2O (0.2 mL). The reaction was stirred at 0° C. for 1 h, and then basified with 30% NaOH to pH=7. The resulting precipitate was collected by filtration to afford the title compound (80 mg), which was used for the next step without further purification. MS (m/z): 353 (M+1)+.

Workup

filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record: ord-6487162e59d04d4e9f88b1fa776943fd
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987269B2

Reaction notes

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