Water → But-2-ynoic acid (2-{6-[3-(2,6-dichloro-3,5-dimethoxy-phenyl)-1-methyl-ureido]-pyrimidin-4-ylamino}-phenyl)-amide

HRID 58160Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 58160
C(OC(=O)[N:7]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[NH2:45])[C:8]1[CH:13]=[C:12]([N:14]([CH3:38])[C:15]([N:17]([C:26]2[C:31]([Cl:32])=[C:30]([O:33][CH3:34])[CH:29]=[C:28]([O:35][CH3:36])[C:27]=2[Cl:37])COCC[Si](C)(C)C)=[O:16])[N:11]=[CH:10][N:9]=1)(C)(C)C.C1CCC(N=C=NC2CCCCC2)CC1.[C:62](O)(=[O:66])[C:63]#[C:64][CH3:65].O>C(Cl)Cl>[Cl:37][C:27]1[C:28]([O:35][CH3:36])=[CH:29][C:30]([O:33][CH3:34])=[C:31]([Cl:32])[C:26]=1[NH:17][C:15](=[O:16])[N:14]([C:12]1[N:11]=[CH:10][N:9]=[C:8]([NH:7][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[NH:45][C:62](=[O:66])[C:63]#[C:64][CH3:65])[CH:13]=1)[CH3:38]

Komponenten

6

Edukt 4

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 685352-Butynoic acidHCID 131736978(2-Amino-phenyl)-{6-[3-(2,6-dichloro-3,5-dimethoxy-phenyl)-1-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-ureido]-pyrimidin-4-yl}-carbamic acid tert-butyl ester

Produkt 1

HCID 118029145But-2-ynoic acid (2-{6-[3-(2,6-dichloro-3,5-dimethoxy-phenyl)-1-methyl-ureido]-pyrimidin-4-ylamino}-phenyl)-amideAusbeute 50,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of (2-amino-phenyl)-{6-[3-(2,6-dichloro-3,5-dimethoxy-phenyl)-1-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-ureido]-pyrimidin-4-yl}-carbamic acid tert-butyl ester (50 g, 0.075 mmol) and DCC (42 g, 0.2 mmol) in DCM (50 mL) was added a solution of but-2-ynoic acid (13 g, 0.15 mmol) in DCM (10 mL) at 0° C., and the resulting mixture was stirred at room temperature overnight. Water (1 mL) was added to quench the reaction. The mixture was concentrated and the residue was purified by reverse phase chromatography to obtain the title compound (20 mg, yield: 34%). MS (ESI): 659 [M+H]+.

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. concentrationThe mixture was concentrated
  4. customthe residue was purified by reverse phase chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0795b596c5a64f4eb8c95eb2bdddb6ac
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434697B2

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