Sodium Carbonate → HCID 57788003, compound

HRID 249977Notes

Reaction equation

HRID 249977 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:19]=[CH:18][C:17]([S:20]([CH3:28])(=[N:22]C(OCC)=O)=[O:21])=[CH:16][CH:15]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:29][CH:30]([CH3:32])[CH3:31].[O-]CC.[Na+].C(=O)([O-])[O-].[Na+].[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]=[CH:16][C:17]([S:20]([CH3:28])(=[NH:22])=[O:21])=[CH:18][CH:19]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:29][CH:30]([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2723922Sodium ethoxideHCID 57788008HCID 57788008, compound

Product 1

HCID 57788003HCID 57788003, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

(RS)-S-[4-({[6-Bromo-4-(isopropylamino)quinazolin-7-yl]oxy}methyl)phenyl]-N-(ethoxycarbonyl)-S-methylsulphoximide (37 mg, 0.07 mmol) is dissolved in ethanol (5 ml), treated with sodium ethoxide (16 mg, 0.26 mmol), and is stirred at 60° C. for 6 hours and subsequently stirred at room temperature overnight. The batch is added to dilute aqueous sodium carbonate solution and extracted with ethyl acetate. The combined organic phases are dried over sodium sulphate and concentrated. The desired product is obtained after chromatographic purification (silica gel, dichloro-methane/methanol: 020% methanol) of the residue in 79% yield (25 mg)

Workup

  1. stirringsubsequently stirred at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-26be3cf757c64a69b2e2f364083b074a
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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