Sodium Bicarbonate → HCID 57788035, compound

HRID 249966Notes

Reaction equation

HRID 249966 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][CH3:31].[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][CH3:31]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723922Sodium ethoxideHCID 57787999HCID 57787999, compound

Product 1

HCID 57788035HCID 57788035, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

According to GWP 6, (RS)-S-[3-({[6-bromo-4-(ethylamino)quinazolin-7-yl]oxy}methyl)-phenyl]-N-(ethoxycarbonyl)-S-methylsulphoximide (38 mg, 0.075 mmol) is dissolved in ethanol (5 mL), admixed with sodium ethoxide (19 mg, 0.27 mmol) and stirred at 60° C. for 3 hours. The reaction solution is admixed with saturated sodium bicarbonate solution and extracted with ethyl acetate. After drying of the organic phase over sodium sulphate and removal of the solvent, the residue is subsequently stirred up with methanol and the crystals are filtered off with suction to obtain the desired product in 45% yield (33 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialAfter drying of the organic phase over sodium sulphate and removal of the solvent
  3. stirringthe residue is subsequently stirred up with methanol
  4. filtrationthe crystals are filtered off with suction

Sources & evidence

ORD record
ord-7324ef19a76b4ebdadf6643ab65bd7e8
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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