Sodium Bicarbonate → HCID 178433829, compound

HRID 384299Notes

Reaction equation

HRID 384299 reaction equation
[NH2:1][C:2]1[C:3]([OH:18])=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([OH:17])=[O:16])[CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.[N:19]([O-])=O.[Na+].[CH3:23][C:24]1[CH2:25][C:26](=[O:39])[N:27]([C:29]2[CH:38]=[CH:37][C:36]3[CH2:35][CH2:34][CH2:33][CH2:32][C:31]=3[CH:30]=2)[N:28]=1.C(=O)(O)[O-].[Na+]>Cl.C(O)C>[F:8][C:6]1[CH:7]=[C:2]([NH:1][N:19]=[C:25]2[C:26](=[O:39])[N:27]([C:29]3[CH:38]=[CH:37][C:36]4[CH2:35][CH2:34][CH2:33][CH2:32][C:31]=4[CH:30]=3)[N:28]=[C:24]2[CH3:23])[C:3]([OH:18])=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([OH:17])=[O:16])[CH:10]=2)[CH:5]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 210723153'-Amino-5'-fluoro-2'-hydroxy-biphenyl-3-carboxylic acidHCID 23668193Sodium NitriteHCID 510365803-Methyl-1-(5,6,7,8-tetrahydronaphthalen-2-yl)-1H-pyrazol-5(4H)-one

Product 1

HCID 178433829HCID 178433829, compoundYield 13.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

Upon cooling by an ice-water bath, 3′-amino-5′-fluoro-2′-hydroxy-biphenyl-3-carboxylic acid 2f (250 mg, 1.01 mmol) was dissolved in 10 mL of hydrochloric acid (1 N) followed by addition of 10 mL of aqueous sodium nitrite (77 mg, 1.12 mmol) and 5-methyl-2-(5,6,7,8-tetrahydro-naphthalen-2-yl)-2,4-dihydro-pyrazol-3-one 4i (230 mg, 1.01 mmol). The mixture was adjusted to pH 8 with saturated aqueous sodium bicarbonate, followed by addition of 10 mL of ethanol. The reaction was warmed up to room temperature overnight and monitored by TLC until the disappearance of the starting materials. The mixture was filtered, dried and recrystallized from methanol to obtain the title compound 5′-fluoro-2′-hydroxy-3′-{N′-[3-methyl-5-oxo-1-(5,6,7,8-tetrahydro-naphthalen-2-yl)-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-biphenyl-3-carboxylic acid 4 (64 mg, yield 13.1%) as a red solid.

Workup

  1. temperatureUpon cooling by an ice-water bath
  2. filtrationThe mixture was filtered
  3. customdried
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-0767224f66574e67bd6d980515277809
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

Loading…