Sodium ethoxide → HCID 44197559, compound

HRID 249936Notes

Reaction equation

HRID 249936 reaction equation
C(OC([N:6]=[S:7]([C:10]1[CH:11]=[C:12]([CH:34]=[CH:35][CH:36]=1)[CH2:13][O:14][C:15]1[CH:24]=[C:23]2[C:18]([C:19]([NH:25][CH:26]([CH3:28])[CH3:27])=[N:20][CH:21]=[N:22]2)=[CH:17][C:16]=1[C:29]([O:31]CC)=[O:30])([CH3:9])=[O:8])=O)C.[O-]CC.[Na+]>>[CH:26]([NH:25][C:19]1[C:18]2[C:23](=[CH:24][C:15]([O:14][CH2:13][C:12]3[CH:34]=[CH:35][CH:36]=[C:10]([S:7]([CH3:9])(=[NH:6])=[O:8])[CH:11]=3)=[C:16]([C:29]([OH:31])=[O:30])[CH:17]=2)[N:22]=[CH:21][N:20]=1)([CH3:28])[CH3:27]

Participants

3

Reactant 2

HCID 2723922Sodium ethoxideHCID 44197558HCID 44197558, compound

Product 1

HCID 44197559HCID 44197559, compoundYield 35%

Procedure

According to GWP 6, ethyl 7-({(RS)-3-[N-(ethoxycarbonyl)-S-methylsulphonimidoyl]-benzyl}oxy)-4-(isopropylamino)quinazoline-6-carboxylate (100 mg, 0.194 mmol) is reacted at 80° C. for 2 hours with sodium ethoxide (59 mg, 0.9 mmol). The reaction mixture is concentrated to dryness. The residue is taken up in ethyl acetate and water and acidified. The organic phase is separated off and subsequently concentrated. After chromatographic purification, the desired product is obtained in 35% yield (28 mg).

Workup

  1. concentrationThe reaction mixture is concentrated to dryness
  2. customThe organic phase is separated off
  3. concentrationsubsequently concentrated
  4. customAfter chromatographic purification

Sources & evidence

ORD record
ord-6a511d69626344658e99a5ff67795ca4
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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