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Dichloromethane → HSD Inhibitor 23

HRID 386518
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 386518
[CH3:1][C:2]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][N:14]=2)[CH2:9][CH2:8]1)([CH3:6])[C:3](O)=[O:4].O.[OH:24][C:25]1[C:33]2N=NN[C:29]=2[CH:28]=[CH:27][CH:26]=1.Cl.CN(C)[CH2:37][CH2:38][CH2:39][N:40]=C=NCC.[CH2:46](Cl)Cl>CCN(C(C)C)C(C)C>[CH3:6][C:2]([N:7]1[CH2:8][CH2:9][N:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:22])[F:21])=[CH:15][N:14]=2)[CH2:11][CH2:12]1)([C:3]([NH:40][CH:39]1[CH:27]2[CH2:26][C:25]3([OH:24])[CH2:37][CH:38]1[CH2:46][CH:29]([CH2:33]3)[CH2:28]2)=[O:4])[CH3:1]
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Komponenten

6

Edukt 4

HCID 6344Dichloromethane2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 16100379HCID 16100379, VerbindungHCID 178526939HCID 178526939, Verbindung

Produkt 1

HCID 11634114HSD Inhibitor 23

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 81531
Diisopropylethylamine
Lösungsmittel

Versuchsvorschrift

A solution of 2-methyl-2-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-propionic acid (159 mg, 0.5 mmoles) from Example 14C in DCM (5 mL) and DIPEA (0.5 mL) was treated with hydroxybenzotriazole hydrate (HOBt) (84 mg, 0.6 mmoles), 5-hydroxy-2-adamantamine (100 mg, 0.6 mmoles) from Example 13A and 15 minutes later with (3-dimethylaminopropyl)-3-ethylcarbodiimide HCl (EDCI) (115 mg, 0.6 mmoles). The mixture was stirred overnight at room temperature after which the DCM was removed under reduced pressure and the residue was partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organic extracts washed with saturated sodium bicarbonate, water, dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and the crude product purified (silica gel, 10-40% acetone in hexane) to provide the title compound as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.41 (s, 1H), 7.67 (m, 2H), 6.66 (d, J=9.1 Hz, 1H), 4.0 (d, J=7.8 Hz, 1H), 3.66 (m, 4H), 2.64 (m, 4H), 2.23-2.1 (m, 3H), 1.9-1.63 (m, 10H), 1.25 (s, 6H); MS (APCI+) m/z 467 (M+H)+.

Aufarbeitung

  1. customwas removed under reduced pressure
  2. customthe residue was partitioned between water and ethyl acetate
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic extracts washed with saturated sodium bicarbonate, water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe crude product purified (silica gel, 10-40% acetone in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-b97e294af9714a44b23253929576cc63
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08372841B2

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