Trifluoroacetic acid → 5-(1-Methyl-1H-pyrazol-4-yl)-3-(quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyridin-7-amine

HRID 876859Notes

Reaction equation

[NH2:1][C:2]1[C:3]([NH:22][CH2:23][C:24]2[CH:25]=[C:26]3[C:31](=[CH:32][CH:33]=2)[N:30]=[CH:29][CH:28]=[CH:27]3)=[N:4][C:5]([C:16]2[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=2)=[CH:6][C:7]=1[NH:8]C(=O)OC(C)(C)C.[N:34]([O-])=O.[Na+].[OH-].[Na+].C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[Na+].[Na+]>O.C(O)(=O)C>[CH3:21][N:19]1[CH:20]=[C:16]([C:5]2[N:4]=[C:3]3[N:22]([CH2:23][C:24]4[CH:25]=[C:26]5[C:31](=[CH:32][CH:33]=4)[N:30]=[CH:29][CH:28]=[CH:27]5)[N:34]=[N:1][C:2]3=[C:7]([NH2:8])[CH:6]=2)[CH:17]=[N:18]1

Participants

Conditions

Temperature: 0 °C

Procedure

tert-Butyl 3-amino-6-(1-methyl-1H-pyrazol-4-yl)-2-(quinolin-6-ylmethylamino)pyridin-4-ylcarbamate (890 mg, 2 mmol) was added to a solution of acetic acid (5 mL) and water (5 mL) at 0° C., followed by the addition of NaNO2 (300 mg, 4 mmol) in H2O (0.5 mL). The reaction was stirred at 0° C. for 1 h, then basified with 30% NaOH to pH=8. The resulting mixture was filtered to afford a solid. The solid was treated with TFA (3 mL), and then stirred at room temperature for another 0.5 h, before treated with aqueous Na2CO3 to adjust the pH to 8. The resulting mixture was purified by chromatography to afford the title compound (190 mg). MS: 358 (M+1)+.

Workup

filtrationThe resulting mixture was filtered
customto afford a solid
stirringstirred at room temperature for another 0.5 h
customThe resulting mixture was purified by chromatography

Sources & evidence

ORD record: ord-5e285e644615434cb2d9911abf129418
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987269B2

Reaction notes

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