Sodium Carbonate → HCID 68840366, compound

HRID 660736Notes

Reaction equation

HRID 660736 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13](I)[CH:12]=[CH:11][C:10]=1[N:16]1[S:20](=[O:22])(=[O:21])[NH:19][C:18](=[O:23])[CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:24]1[CH:28]=[C:27](B(O)O)[CH:26]=[N:25]1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:27]2[CH:28]=[N:24][NH:25][CH:26]=2)[CH:12]=[CH:11][C:10]=1[N:16]1[S:20](=[O:22])(=[O:21])[NH:19][C:18](=[O:23])[CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 177502781H-Pyrazole-4-boronic acidHCID 688386435-(2-Benzyloxy-4-iodophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Product 1

HCID 68840366HCID 68840366, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (100 mg, 0.225 mmol), 4-pyrazoleboronic acid (87 mg, 0.45 mmol), resin-bound PPh3Pd (346 mg, loading 0.13 mmol/g) and aqueous Na2CO3 (0.45 mL of a 2M solution) in DME (3 mL) is heated in a microwave apparatus at 110° C. for 30 min. The mixture is filtered and the solvent removed under reduced pressure. The residue is purified by reverse phase MPLC to give the title compound.

Workup

  1. filtrationThe mixture is filtered
  2. customthe solvent removed under reduced pressure
  3. customThe residue is purified by reverse phase MPLC

Sources & evidence

ORD record
ord-417d847b2db141fcab281a71043fce12
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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