Sodium ethoxide → HCID 57787998, compound

HRID 249972Notes

Reaction equation

HRID 249972 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:32])(=[N:26]C(OCC)=O)=[O:25])[CH:19]=1)[N:12]=[CH:11][N:10]=[C:9]2[NH:33][C:34]1[S:35][CH:36]=[CH:37][N:38]=1)=[O:5])[CH3:2].[O-]CC.[Na+]>>[CH3:32][S:24]([C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[CH2:17][O:16][C:15]1[CH:14]=[C:13]2[C:8]([C:9]([NH:33][C:34]3[S:35][CH:36]=[CH:37][N:38]=3)=[N:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5])(=[NH:26])=[O:25]

Participants

3

Reactant 2

HCID 2723922Sodium ethoxideHCID 57787961HCID 57787961, compound

Product 1

HCID 57787998HCID 57787998, compoundYield 42%

Procedure

According to GWP 6, ethyl-7-({(RS)-3-[N-(ethoxycarbonyl)-S-methyl-sulphonimidoyl]-benzyl}oxy)-4-(thiazol-2-ylamino)quinazoline-6-carboxylate (175 mg, 0.182 mmol) is reacted at 80° C. for 2 hours with sodium ethoxide (55 mg, 0.8 mmol). After cooling, 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 desired product is obtained after chromatographic purification (silica gel, dichloromethane/methanol: 9/1) in 42% yield (39 mg).

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture is concentrated to dryness
  3. customThe organic phase is separated off
  4. dry with materialdried over sodium sulphate
  5. concentrationsubsequently concentrated

Sources & evidence

ORD record
ord-d3bcf9db06d942e8a36ac32810d82e66
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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