Sodium Bicarbonate → HCID 178433801, compound

HRID 384391Notes

Reaction equation

HRID 384391 reaction equation
Br.[OH:2][C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C:10]1[S:11][C:12]([CH3:18])=[C:13]([C:15]([OH:17])=[O:16])[N:14]=1.[N:19]([O-])=O.[Na+].[CH2:23]1[C:31]2[C:26](=[CH:27][C:28]([N:32]3[C:36](=[O:37])[CH2:35][C:34]([CH3:38])=[N:33]3)=[CH:29][CH:30]=2)[CH2:25][CH2:24]1.C(=O)(O)[O-].[Na+]>Cl>[OH:2][C:3]1[C:8]([NH:9][N:19]=[C:35]2[C:36](=[O:37])[N:32]([C:28]3[CH:27]=[C:26]4[C:31](=[CH:30][CH:29]=3)[CH2:23][CH2:24][CH2:25]4)[N:33]=[C:34]2[CH3:38])=[CH:7][CH:6]=[CH:5][C:4]=1[C:10]1[S:11][C:12]([CH3:18])=[C:13]([C:15]([OH:17])=[O:16])[N:14]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 574837802-Indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-oneHCID 136117081HCID 136117081, compound

Product 1

HCID 178433801HCID 178433801, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2-(2-Hydroxy-3-amino-phenyl)-5-methyl-thiazole-4-carboxylic acid hydrobromide 47c (200 mg, 0.60 mmol) was dissolved in 2 mL of hydrochloric acid (1 N) upon cooling by an ice-water bath, followed by dropwise addition of 0.82 mL of aqueous sodium nitrite (46 mg, 0.66 mmol). After the mixture was stirred for 20 minutes, 2-indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-one 1i (116 mg, 0.544 mmol) was added. The mixture was adjusted to pH 8˜9 by batch addition of saturated aqueous sodium bicarbonate (781 mg, 9.3 mmol). Then 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 20 mL of water. The mixture was adjusted to pH 3˜4 with concentrated hydrochloric acid. The mixture was filtered and the filter cake was dried and purified by HPLC to obtain the title compound 2-{2-hydroxy-3-[N′-(1-indan-5-yl-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene)-hydrazino]-phenyl}-5-methyl-thiazole-4-carboxylic acid 47 (195 mg, yield 75.9%) as a red solid.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. customThen the generated bubbles were quenched with 2 mL of ethanol
  3. customreacted overnight
  4. filtrationThe mixture was filtered
  5. dissolutionthe filter cake was dissolved in 20 mL of water
  6. filtrationThe mixture was filtered
  7. customthe filter cake was dried
  8. custompurified by HPLC

Sources & evidence

ORD record
ord-14321b6d8c214ebf8b142965e1fcaa63
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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