1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 1-({4-[(2-Fluoro-4-iodophenyl)amino]-3-thienyl}carbonyl)-3-(hydroxymethyl)azetidin-3-ol

HRID 605752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 605752
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([C:15]([OH:17])=O)=[CH:12][S:13][CH:14]=1.Cl.CN(C)CCCN=C=NCC.Cl.[OH:31][CH2:32][C:33]1([OH:37])[CH2:36][NH:35][CH2:34]1>CN(C)C1C=CN=CC=1.CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([C:15]([N:35]2[CH2:36][C:33]([CH2:32][OH:31])([OH:37])[CH2:34]2)=[O:17])=[CH:12][S:13][CH:14]=1

Komponenten

6

Edukt 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 552884783-(Hydroxymethyl)azetidin-3-ol hydrochlorideHCID 666174654-[(2-Fluoro-4-iodophenyl)amino]thiophene-3-carboxylic acid

Produkt 1

HCID 670515741-({4-[(2-Fluoro-4-iodophenyl)amino]-3-thienyl}carbonyl)-3-(hydroxymethyl)azetidin-3-olAusbeute 106,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-[(2-fluoro-4-iodophenyl)amino]thiophene-3-carboxylic acid (200 mg, 0.551 mmol), 4-(dimethylamino)pyridine (202 mg, 1.65 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (127 mg, 0.662 mmol) were dissolved in DMF (3 mL). The mixture was stirred at ambient for 5 minutes and then 3-(hydroxymethyl)azetidin-3-ol hydrochloride (72 mg, 0.516 mmol) was added and the mixture was stirred for 15 h. The mixture was partitioned between ethyl acetate and 20% citric acid. The aqueous portion was extracted with ethyl acetate. The combined organic portion was washed with 5% lithium chloride, saturated sodium bicarbonate and brine, then was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was crystallized from dichloromethane to afford 1-({4-[(2-fluoro-4-iodophenyl)amino]-3-thienyl}carbonyl)-3-(hydroxymethyl)azetidin-3-ol (247 mg, 0.551 mmol, quantitative yield) as off-white crystals: MS (EI) for C15H14FIN2O3S: 449 (MH+).

Aufarbeitung

  1. stirringthe mixture was stirred for 15 h
  2. customThe mixture was partitioned between ethyl acetate and 20% citric acid
  3. extractionThe aqueous portion was extracted with ethyl acetate
  4. washThe combined organic portion was washed with 5% lithium chloride, saturated sodium bicarbonate and brine
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was crystallized from dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-eced9430cf3c4c5a8a74cfaf6d7c944c
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915250B2

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