Sodium ethoxide → HCID 57787981, compound

HRID 249971Notes

Reaction equation

HRID 249971 reaction equation
C(OC([N:6]=[S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][O:17][C:18]2[CH:27]=[C:26]3[C:21]([C:22]([NH:28][CH:29]([CH3:31])[CH3:30])=[N:23][CH:24]=[N:25]3)=[CH:20][CH:19]=2)[CH:11]=1)([CH3:9])=[O:8])=O)C.[O-]CC.[Na+]>>[CH:29]([NH:28][C:22]1[C:21]2[C:26](=[CH:27][C:18]([O:17][CH2:16][C:12]3[CH:11]=[C:10]([S:7]([CH3:9])(=[NH:6])=[O:8])[CH:15]=[CH:14][CH:13]=3)=[CH:19][CH:20]=2)[N:25]=[CH:24][N:23]=1)([CH3:31])[CH3:30]

Participants

3

Reactant 2

HCID 2723922Sodium ethoxideHCID 57787970HCID 57787970, compound

Product 1

HCID 57787981HCID 57787981, compoundYield 51%

Procedure

According to GWP 6, (RS)-N-(ethoxycarbonyl)-S-[3-({[4(isopropylamino)quinazolin-7-yl]oxy}methyl)phenyl]-S-methylsulphoximide (68 mg, 0.16 mmol) is reacted with sodium ethoxide (46 mg, 0.68 mmol) at 80° C. for 2 hours. The reaction mixture is concentrated to dryness. The residue is taken up in ethyl acetate and water. The organic phase is separated off, dried over sodium sulphate and subsequently concentrated. The residue is triturated a number of times with diethyl ether and the solvent is subsequently decanted off. The residue is dissolved in dichloromethane and concentrated again. The desired product is obtained in 51% yield (30 mg).

Workup

  1. concentrationThe reaction mixture is concentrated to dryness
  2. customThe organic phase is separated off
  3. dry with materialdried over sodium sulphate
  4. concentrationsubsequently concentrated
  5. customThe residue is triturated a number of times with diethyl ether
  6. customthe solvent is subsequently decanted off
  7. dissolutionThe residue is dissolved in dichloromethane
  8. concentrationconcentrated again

Sources & evidence

ORD record
ord-b92e8f33eb344d269d59e610d96ae463
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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