Acetic Acid → HCID 178480088, compound

HRID 876854Notes

Reaction equation

HRID 876854 reaction equation
[NH2:1][C:2]1[C:3]([NH:15][CH2:16][C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]=[CH:22][CH:21]=[CH:20]3)=[N:4][C:5]([C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)=[CH:6][C:7]=1[OH:8].C(O)(=O)C.[N:31]([O-])=O.[Na+].[OH-].[Na+]>O>[CH3:14][N:12]1[CH:13]=[C:9]([C:5]2[N:4]=[C:3]3[N:15]([CH2:16][C:17]4[CH:18]=[C:19]5[C:24](=[CH:25][CH:26]=4)[N:23]=[CH:22][CH:21]=[CH:20]5)[N:31]=[N:1][C:2]3=[C:7]([OH:8])[CH:6]=2)[CH:10]=[N:11]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 178480090HCID 178480090, compound

Product 1

HCID 178480088HCID 178480088, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

3-amino-6-(1-methyl-1H-pyrazol-4-yl)-2-(quinolin-6-ylmethylamino)pyridin-4-ol (170 mg, 0.49 mmol) was added to a solution of acetic acid (3 mL) and H2O (3 mL) at 0° C., followed by the addition of NaNO2 (69 mg, 10 mmol) in H2O (0.3 mL). The reaction mixture was stirred at 0° C. for 1 h, then basified with aqueous 30% NaOH to pH=6-7 and purified by chromatography to afford the title compound (120 mg). MS (m/z): 358 (M+1)+.

Workup

  1. custompurified by chromatography

Sources & evidence

ORD record
ord-380663c932b644f0aaec90c36a7c1a3e
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

Loading…