Sodium Bicarbonate → HCID 178433772, compound

HRID 510420Notes

Reaction equation

HRID 510420 reaction equation
C(O)(=O)C.[Cl:5][C:6]1[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:7]=1[CH2:8][C:9]1[C:10]([CH3:25])=[N:11][N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[NH:14][C:13]=12.C(=O)(O)[O-].[Na+]>CO.O>[Cl:5][C:6]1[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:7]=1[CH2:8][C:9]1[C:10]([CH3:25])=[N:11][N:12]2[C:17]([OH:18])=[CH:16][C:15]([C:19]3[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=3)=[N:14][C:13]=12

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 178475921HCID 178475921, compound

Product 1

HCID 178433772HCID 178433772, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of 3-(2,3-dichlorobenzyl)-2-methyl-5-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidin-7(4H)-one acetate (100 mg, 0.225 mmol), sodium bicarbonate (0.5 g) in methanol/water (20 mL/10 mL) was stirred at room temperature overnight. Then the mixture was concentrated. The residue was purified by silica gel column to give the titled product (75 mg, 87%); LC/MS: MS (ES+) m/e 385 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 2.15 (s, 3H), 4.14 (s, 2H), 6.11 (s, 1H), 6.97-7.00 (m, 1H), 7.25 (t, J=8.1 Hz, 1H), 7.48-7.50 (m, 1H), 7.82-7.82 (m, 2H), 8.71-8.74 (m, 2H), 12.20 (s, 1H).

Workup

  1. concentrationThen the mixture was concentrated
  2. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-b652b2edce2a44e29e4dbd1adf92ce00
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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