Diisopropylamine → Methyl 2-(4-(6-chloropyrimidine-4-carboxamido)-3-methylphenylsulfonamido)acetate

HRID 1746674Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1746674
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][C:12]=2[CH3:21])=[O:9])[CH:3]=1.[NH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25].C(NC(C)C)(C)C>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([NH:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])(=[O:19])=[O:18])=[CH:13][C:12]=2[CH3:21])=[O:9])[CH:3]=1

Komponenten

5

Edukt 3

HCID 7912DiisopropylamineHCID 69221Glycine methyl esterHCID 594468454-(6-Chloropyrimidine-4-carboxamido)-3-methylbenzene-1-sulfonyl chloride2×

Produkt 1

HCID 59446920Methyl 2-(4-(6-chloropyrimidine-4-carboxamido)-3-methylphenylsulfonamido)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4-(6-chloropyrimidine-4-carboxamido)-3-methylbenzene-1-sulfonyl chloride (Intermediate 30, 1.2g; 3.47 mmol) in THF (100ml) was treated with methyl 2-aminoacetate (540 mg; 4.34 mmol) and diisopropylamine (2 ml; 14.3 mmol). After stirring at RT for 18 hours the solvent was removed in vacuo and the residue redissolved in DCM and washed with water. The organic extracts were passed through a hydrophobic frit and the solvent removed in vacuo. The residue was purified by column chromatography (silica) eluting with petroleum ether containing increasing amounts of EtOAc. The title product was obtained as a white solid (1.05 g, 76%).

Aufarbeitung

  1. customwas removed in vacuo
  2. dissolutionthe residue redissolved in DCM
  3. washwashed with water
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by column chromatography (silica)
  6. washeluting with petroleum ether containing
  7. temperatureincreasing amounts of EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-a957f8b80e5846e0b5cb416a2415f489
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150519B2

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