Sodium Bicarbonate → HCID 178433830, compound

HRID 384340Notes

Reaction equation

HRID 384340 reaction equation
Br.[NH2:2][C:3]1[C:4]([OH:18])=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([OH:17])=[O:16])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[N:19]([O-])=O.[Na+].[CH3:23][C:24]1[CH2:25][C:26](=[O:42])[N:27]([C:29]2[CH:30]=[C:31]3[C:35](=[CH:36][CH:37]=2)[C:34]([CH3:39])([CH3:38])[CH2:33][C:32]3([CH3:41])[CH3:40])[N:28]=1.C(=O)(O)[O-].[Na+]>Cl.C(O)C>[OH:18][C:4]1[C:3]([NH:2][N:19]=[C:25]2[C:26](=[O:42])[N:27]([C:29]3[CH:30]=[C:31]4[C:35](=[CH:36][CH:37]=3)[C:34]([CH3:39])([CH3:38])[CH2:33][C:32]4([CH3:41])[CH3:40])[N:28]=[C:24]2[CH3:23])=[CH:8][CH:7]=[CH:6][C:5]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([OH:17])=[O:16])[CH:10]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 510369935-Methyl-2-(1,1,3,3-tetramethyl-indan-5-yl)-2,4-dihydro-pyrazol-3-oneHCID 574837893'-Amino-2'-hydroxy-biphenyl-3-carboxylic acid hydrobromide

Product 1

HCID 178433830HCID 178433830, compoundYield 29.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

3′-Amino-2′-hydroxy-biphenyl-3-carboxylic acid hydrobromide 1f (172 mg, 0.56 mmol) was dissolved in 1.9 mL of 1 N hydrochloric acid upon cooling by an ice-water bath, followed by dropwise addition of 0.7 mL of aqueous sodium nitrite (42 mg, 0.61 mmol) and 5-methyl-2-(1,1,3,3-tetramethyl-indan-5-yl)-2,4-dihydro-pyrazol-3-one 19d (135 mg, 0.5 mmol). The mixture was adjusted to pH 8˜9 by batch addition of saturated sodium bicarbonate (700 mg, 8.33 mmol) followed by addition of 2 mL of ethanol. The reaction mixture was warmed up to room temperature 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. 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 2′-hydroxy-3′-{N′-[3-methyl-5-oxo-1-(1,1,3,3-tetramethyl-indan-5-yl)-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-biphenyl-3-carboxylic acid 19 (75 mg, yield 29.4%) as a red solid.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. filtrationThe mixture was filtered
  3. dissolutionthe filter cake was dissolved in 20 mL of water
  4. additionAfter mixing well
  5. filtrationfiltered
  6. customdried
  7. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-5161822ca1a3470e8e668656105c8c8d
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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