Sodium Bicarbonate → HCID 57788017, compound

HRID 249968Notes

Reaction equation

HRID 249968 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][C:14]1[CH:15]=[C:16]([S:20]([CH3:28])(=[N:22]C(OCC)=O)=[O:21])[CH:17]=[CH:18][CH:19]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:29][CH2:30][C@H:31]([OH:33])[CH3:32].[O-]CC.[Na+].C(=O)(O)[O-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][C:14]1[CH:15]=[C:16]([S:20]([CH3:28])(=[NH:22])=[O:21])[CH:17]=[CH:18][CH:19]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:29][CH2:30][C@H:31]([OH:33])[CH3:32]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723922Sodium ethoxideHCID 57788013HCID 57788013, compound

Product 1

HCID 57788017HCID 57788017, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

According to GWP 6, (RS)-S-(3-{[(6-bromo-4-{[(R)-2-hydroxypropyl]amino}quinazolin-7-yl)oxy]methyl}phenyl)-N-(ethoxycarbonyl)-S-methylsulphoximide (38 mg, 0.071 mmol) is dissolved in ethanol (5 mL), admixed with sodium ethoxide (17 mg, 0.25 mmol) and stirred at 60° C. for 6 hours. The reaction solution is admixed with saturated sodium bicarbonate solution and extracted with ethyl acetate. Drying of the organic phase over sodium sulphate and removal of the solvent and also chromatographic purification of the residue (silica gel, dichloromethane/methanol: 0→10% methanol) gives the desired product in 88% yield (29 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialDrying of the organic phase over sodium sulphate and removal of the solvent and also chromatographic purification of the residue (silica gel, dichloromethane/methanol: 0→10% methanol)

Sources & evidence

ORD record
ord-968bfd908dce4928945e0615740e1583
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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