Sodium Bicarbonate → HCID 178480091, compound

HRID 876852Notes

Reaction equation

HRID 876852 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]([NH: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)[C:10]([N+:25]([O-:27])=[O:26])=[C:9](N)[CH:8]=2)[CH:4]=[N:3]1.[NH+]([O-])=[O:30].C([O-])(O)=O.[Na+]>[H+].[B-](F)(F)(F)F.O>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]([NH: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)[C:10]([N+:25]([O-:27])=[O:26])=[C:9]([OH:30])[CH:8]=2)[CH:4]=[N:3]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 673048626-(1-methyl-1H-pyrazol-4-yl)-3-nitro-N2-(quinolin-6-ylmethyl)pyridine-2,4-diamineHCID 178526385HCID 178526385, compound

Product 1

HCID 178480091HCID 178480091, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 28118Tetrafluoroboric acidSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 6-(1-methyl-1H-pyrazol-4-yl)-3-nitro-N2-(quinolin-6-ylmethyl)pyridine-2,4-diamine (260 mg, 0.69 mmol) in HBF4 (5 mL) at 0° C. was added HNO2 (96 mg, 1.4 mmol) in H2O (0.5 mL). The reaction mixture was stirred at 0° C. overnight, then basified with aqueous NaHCO3 to pH=6-7. The resulting mixture was filtered. The filtrate was concentrated and purified by chromatography on silica gel to afford the title compound (200 mg). MS (m/z): 377 (M+1)+.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationThe filtrate was concentrated
  3. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-788d9a6b796146a3a302bb01f15db626
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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