Ethylamine → N,N'-diethyl-2-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]pentanediamide

HRID 1402587Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1402587
[F:1][C:2]1[CH:31]=[CH:30][C:29]([C:32]([NH:34][C:35]2[CH:40]=[C:39]([CH3:41])[CH:38]=[CH:37][C:36]=2[F:42])=[O:33])=[CH:28][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2[NH:15][CH:14]=[C:13]([C:16]([NH:18][CH:19]([CH2:23][CH2:24][C:25]([OH:27])=O)[C:20](O)=[O:21])=[O:17])[CH:12]=2)[CH:6]=1.Cl.C[N:45](C)[CH2:46][CH2:47]CN=C=NCC.[CH2:55]([NH2:57])[CH3:56].C1COCC1>CN(C=O)C.O>[CH2:55]([NH:57][C:20](=[O:21])[CH:19]([NH:18][C:16]([C:13]1[CH:12]=[C:11]([C:7]2[CH:6]=[C:5]([O:4][C:3]3[CH:28]=[C:29]([C:32]([NH:34][C:35]4[CH:40]=[C:39]([CH3:41])[CH:38]=[CH:37][C:36]=4[F:42])=[O:33])[CH:30]=[CH:31][C:2]=3[F:1])[CH:10]=[CH:9][N:8]=2)[NH:15][CH:14]=1)=[O:17])[CH2:23][CH2:24][C:25]([NH:45][CH2:46][CH3:47])=[O:27])[CH3:56]

Komponenten

7

Edukt 4

HCID 6341EthylamineHCID 8028TetrahydrofuranHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 712935772-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]pentanedioic acid

Produkt 1

HCID 71293595N,N'-diethyl-2-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]pentanediamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]pentanedioic acid (100 mg, 0.17 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC, 83 mg, 0.43 mmol) in 10 ml of anhydrous DMF was added 2M ethylamine solution in THF (0.43 ml, 0.86 mmol). The mixture was stirred at room temperature for overnight and poured into 100 ml of water. The precipitates were filtered, washed with water and dried in vacuo to give the crude, which was purified by silica gel chromatography eluting with 5-8% of methanol in chloroform to afford N,N′-diethyl-2-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]pentanediamide as white solid. Yield: 76 mg, 69%.

Aufarbeitung

  1. filtrationThe precipitates were filtered
  2. washwashed with water
  3. customdried in vacuo
  4. customto give the crude, which
  5. customwas purified by silica gel chromatography
  6. washeluting with 5-8% of methanol in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-8012355d0b9c43d3874614198388f016
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906944B2

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