Sodium ethoxide → HCID 57787987, compound

HRID 249950Notes

Reaction equation

HRID 249950 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][CH2:31][OH:32].[O-]CC.[Na+]>C(O)C.[Cl-].[Na+].O>[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][CH2:31][OH:32]

Participants

5

Reactant 2

HCID 2723922Sodium ethoxideHCID 57787995HCID 57787995, compound

Product 1

HCID 57787987HCID 57787987, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

According to GWP 6, (RS)-S-[3-({[6-bromo-4-(2-hydroxyethylamino)quinazolin-7-yl]oxy}methyl)phenyl]-N-(ethoxycarbonyl)-S-methylsulphoximide (67 mg, 0.13 mmol) is reacted with sodium ethoxide (29 mg, 0.46 mmol) in ethanol (3 mL). After cooling to room temperature, the reaction mixture is admixed with brine and stirred for 30 minutes and the resulting precipitate is filtered off with suction to leave the desired product in 81% yield (47 mg).

Workup

  1. filtrationthe resulting precipitate is filtered off with suction

Sources & evidence

ORD record
ord-bc655f501b974a63ab42bed2d7040728
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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