Sodium Bicarbonate → HCID 57787973, compound

HRID 249967Notes

Reaction equation

HRID 249967 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 57787974HCID 57787974, compound

Product 1

HCID 57787973HCID 57787973, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

According to GWP 6, (RS)-S-(3-{[(6-bromo-4-{[(S)-2-hydroxypropyl]amino}quinazolin-7-yl)oxy]methyl}phenyl)-N-(ethoxycarbonyl)-S-methylsulphoximide (39 mg, 0.073 mmol) is dissolved in ethanol (5 mL), admixed with sodium ethoxide (18 mg, 0.26 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 86% 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-5e2bfe87aae64e758c05769ff273d8d0
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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