1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 3-hydroxy-adamantane-1-carboxylic acid (5,6-dihydro-4H-cyclopentathiazol-2-yl)-amide

HRID 1470044

Reaktionsgleichung

Reaktionsgleichung von HRID 1470044
Cl.[S:2]1[C:6]2[CH2:7][CH2:8][CH2:9][C:5]=2[N:4]=[C:3]1[NH2:10].[OH:11][C:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][C:14]([C:22](O)=[O:23])([CH2:15]3)[CH2:13]1)[CH2:19]2.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[S:2]1[C:6]2[CH2:7][CH2:8][CH2:9][C:5]=2[N:4]=[C:3]1[NH:10][C:22]([C:14]12[CH2:15][CH:16]3[CH2:17][CH:18]([CH2:19][C:12]([OH:11])([CH2:21]3)[CH2:13]1)[CH2:20]2)=[O:23]

Komponenten

7

Edukt 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27365183-Hydroxyadamantane-1-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 162532465,6-Dihydro-4H-cyclopenta[d]thiazol-2-amine hydrochloride

Produkt 1

HCID 871864543-hydroxy-adamantane-1-carboxylic acid (5,6-dihydro-4H-cyclopentathiazol-2-yl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of Example 209A (921 mg, 5.19 mmol), 3-hydroxy-adamantane-1-carboxylic acid (1.22 g, 6.2 mmol), 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (2.0 g, 10.4 mmol), 1-hydroxybenzotriazole hydrate (846 mg, 10.4 mmol) and 4-dimethylaminopyridine (196 mg, 1.04 mmol) in pyridine (20 mL) was stirred at room temperature for 12 hours. The solvent was removed and the residue was diluted with water and extracted with ethyl acetate. The organic extract was dried (Na2SO4), filtered and concentrated. Purification by flash chromatography (silica gel, 50% ethyl acetate/hexanes) afforded the title compound. MS (ESI) m/z 319 (M+H)+.

Aufarbeitung

  1. customThe solvent was removed
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. dry with materialwas dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash chromatography (silica gel, 50% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8ed247fa01d44a269291973c15e35436
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006275B2

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