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Hydrochloric Acid → 1-(2,3-Dihydroxy-propyl)-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-1,2,3,5-tetrahydro-imidazo[1,2-a]pyridin-8-yl]-amide

HRID 1259378
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1259378
Cl.C(OC([N:9]1[C:13]2=[C:14]([NH:29][S:30]([C:33]3([CH2:36][CH:37]([OH:40])[CH2:38][OH:39])[CH2:35][CH2:34]3)(=[O:32])=[O:31])[C:15]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=3[F:28])=[C:16]([CH3:19])[C:17](=[O:18])[N:12]2[CH2:11][CH2:10]1)=O)(C)(C)C.CO>C1COCC1.C(Cl)(Cl)Cl>[F:28][C:22]1[CH:23]=[C:24]([I:27])[CH:25]=[CH:26][C:21]=1[NH:20][C:15]1[C:14]([NH:29][S:30]([C:33]2([CH2:36][CH:37]([OH:40])[CH2:38][OH:39])[CH2:34][CH2:35]2)(=[O:31])=[O:32])=[C:13]2[NH:9][CH2:10][CH2:11][N:12]2[C:17](=[O:18])[C:16]=1[CH3:19]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 671938308-[1-(2,3-Dihydroxy-propyl)-cyclopropanesulfonylamino]-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-imidazo[1,2-a]pyridine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 529347851-(2,3-Dihydroxy-propyl)-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-1,2,3,5-tetrahydro-imidazo[1,2-a]pyridin-8-yl]-amideAusbeute 14,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Concentrated HCl (3 mL) was added to a stirred solution of 8-[1-(2,3-dihydroxy-propyl)-cyclopropanesulfonylamino]-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-imidazo[1,2-a]pyridine-1-carboxylic acid tert-butyl ester (80 mg) in THF (5 mL). The resulting mixture was stirred at 40° C. for 2 hours. The reaction was monitored by TLC (15% MeOH in CHCl3). The reaction mixture was concentrated and partitioned between ethylacetate and water. The organic layer was washed with saturated NaHCO3 solution and concentrated to afford the crude product. Purification by column chromatography on silica gel (5% methanol in CHCl3), followed by preparative HPLC afforded 10 mg of the product (14.7% yield)

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between ethylacetate and water
  3. washThe organic layer was washed with saturated NaHCO3 solution
  4. concentrationconcentrated
  5. customto afford the crude product
  6. customPurification by column chromatography on silica gel (5% methanol in CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-4dfe87bb825c42e9956d5e4c40665051
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08466289B2

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