Sodium Bicarbonate → HCID 178433842, compound

HRID 384362Notes

Reaction equation

HRID 384362 reaction equation
Br.[NH2:2][C:3]1[C:4]([OH:18])=[C:5]([C:10]2[S:14][C:13]([C:15]([OH:17])=[O:16])=[CH:12][CH:11]=2)[CH:6]=[C:7]([CH3:9])[CH:8]=1.[N:19]([O-])=O.[Na+].[CH3:23][C:24]1([CH3:40])[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([N:33]3[C:37](=[O:38])[CH2:36][C:35]([CH3:39])=[N:34]3)[CH:31]=2)[CH2:26][CH2:25]1.C(=O)(O)[O-].[Na+]>Cl.C(O)C>[CH3:23][C:24]1([CH3:40])[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([N:33]3[C:37](=[O:38])[C:36](=[N:19][NH:2][C:3]4[C:4]([OH:18])=[C:5]([C:10]5[S:14][C:13]([C:15]([OH:17])=[O:16])=[CH:12][CH:11]=5)[CH:6]=[C:7]([CH3:9])[CH:8]=4)[C:35]([CH3:39])=[N:34]3)[CH:31]=2)[CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 510369942-(3,3-Dimethyl-indan-5-yl)-5-methyl-2,4-dihydro-pyrazol-3-oneHCID 574838215-(3-Amino-2-hydroxy-5-methyl-phenyl)-thiophene-2-carboxylic acid hydrobromide

Product 1

HCID 178433842HCID 178433842, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

5-(3-Amino-2-hydroxy-5-methyl-phenyl)-thiophene-2-carboxylic acid hydrobromide 24d (366 mg, 1.11 mmol) was dissolved in 3.7 mL of 1 N hydrochloric acid upon cooling by an ice-water bath, followed by dropwise addition of 1.5 mL of aqueous sodium nitrite (85 mg, 1.22 mmol). After the mixture was reacted for 20 minutes, 2-(3,3-dimethyl-indan-5-yl)-5-methyl-2,4-dihydro-pyrazol-3-one 8i (242 mg, 1 mmol) was added. The mixture was adjusted to pH 8 with saturated aqueous sodium bicarbonate, followed by addition of 2 mL of ethanol. Upon completion of the addition, the ice-water bath was removed. The reaction mixture was reacted overnight at room temperature. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filter cake was added to 30 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 silica gel column chromatography to obtain the title compound 5-(3-{N′-[1-(3,3-dimethyl-indan-5-yl)-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-2-hydroxy-5-methyl-phenyl)-thiophene-2-carboxylic acid 34 (308 mg, yield 61.4%) as a red solid.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. customAfter the mixture was reacted for 20 minutes
  3. additionUpon completion of the addition
  4. customthe ice-water bath was removed
  5. customThe reaction mixture was reacted overnight at room temperature
  6. filtrationThe mixture was filtered
  7. additionthe filter cake was added to 30 mL of water
  8. filtrationThe mixture was filtered
  9. customthe filter cake was dried
  10. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-e7d2c3f2d6464e66a8b559a2ebf502ea
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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