Sodium Bicarbonate → HCID 178433841, compound

HRID 384334Notes

Reaction equation

HRID 384334 reaction equation
Cl.[NH2:2][C:3]1[C:4]([OH:19])=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([OH:18])=[O:17])[CH:11]=2)[CH:6]=[C:7]([CH3:9])[CH:8]=1.[N:20]([O-])=O.[Na+].[CH3:24][C:25]1([CH3:41])[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([N:34]3[C:38](=[O:39])[CH2:37][C:36]([CH3:40])=[N:35]3)[CH:32]=2)[CH2:27][CH2:26]1.C(=O)(O)[O-].[Na+]>Cl>[CH3:24][C:25]1([CH3:41])[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([N:34]3[C:38](=[O:39])[C:37](=[N:20][NH:2][C:3]4[C:4]([OH:19])=[C:5]([C:10]5[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([OH:18])=[O:17])[CH:11]=5)[CH:6]=[C:7]([CH3:9])[CH:8]=4)[C:36]([CH3:40])=[N:35]3)[CH:32]=2)[CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 510369942-(3,3-Dimethyl-indan-5-yl)-5-methyl-2,4-dihydro-pyrazol-3-oneHCID 574838093'-Amino-2'-hydroxy-5'-methyl-biphenyl-3-carboxylic acid hydrochloride

Product 1

HCID 178433841HCID 178433841, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

3′-Amino-2′-hydroxy-5′-methyl-biphenyl-3-carboxylic acid hydrochloride 11f (257 mg, 0.92 mmol) was dissolved in 3.1 mL of hydrochloric acid (1 N) upon cooling by an ice-water bath, followed by dropwise addition of 1.2 mL of aqueous sodium nitrite (70 mg, 1.01 mmol). After the mixture was stirred for 20 minutes, 2-(3,3-dimethyl-indan-5-yl)-5-methyl-2,4-dihydro-pyrazol-3-one 8i (200 mg, 0.83 mmol) was added. The mixture was adjusted to pH 8˜9 by batch addition of aqueous sodium bicarbonate (1.157 g, 13.8 mmol). The generated bubbles were quenched with 2 mL of ethanol. The reaction mixture was warmed up to room temperature and reacted overnight. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filter cake was dissolved in 30 mL of water. After mixing well, the mixture was adjusted to pH 3˜4 with concentrated hydrochloric acid, filtered and dried. The crude product was purified by HPLC to obtain the title compound 3′-{N′-[1-(3,3-dimethyl-indan-5-yl)-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-2′-hydroxy-5′-methyl-biphenyl-3-carboxylic acid 16 (160 mg, yield 39.0%) as an orange solid.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. customThe generated bubbles were quenched with 2 mL of ethanol
  3. customreacted overnight
  4. filtrationThe mixture was filtered
  5. dissolutionthe filter cake was dissolved in 30 mL of water
  6. additionAfter mixing well
  7. filtrationfiltered
  8. customdried
  9. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-1925c57b4f0d4bfb949b881987934ec3
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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