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Hydrochloric Acid → 2-(2-(2-(2-((2-Methoxy-4-(piperazin-1-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetamide

HRID 2272395
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2272395
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[N:26]=[C:25]([CH2:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[CH2:35][C:36]([O-:38])=O)[C:24]([C:39]([F:42])([F:41])[F:40])=[CH:23][N:22]=3)=[C:16]([O:43][CH3:44])[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[Li+].O[N:47]1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.Cl.C(N(CC)C(C)C)(C)C.C(=O)([O-])[O-].[NH4+].[NH4+]>O1CCCC1.CN(C)C=O>[CH3:44][O:43][C:16]1[CH:15]=[C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:19]=[CH:18][C:17]=1[NH:20][C:21]1[N:26]=[C:25]([CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH2:35][C:36]([NH2:47])=[O:38])[C:24]([C:39]([F:42])([F:40])[F:41])=[CH:23][N:22]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 517111Ammonium CarbonateHCID 71225535Lithium 2-(2-(2-(2-((4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-2-methoxyphenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetate

Produkt 1

HCID 601485632-(2-(2-(2-((2-Methoxy-4-(piperazin-1-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of lithium 2-(2-(2-(2-((4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-2-methoxyphenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetate (I7) (0.352 g, 0.672 mmol), 1-hydroxybenzotriazole (0.093 g, 0.686 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide) hydrochloride (0.121 g, 0.629 mmol) in dry tetrahydrofuran (16 mL) and dimethylformamide (7 mL) was added N,N-diisopropylethylamine (0.498 mL, 2.86 mmol) under a nitrogen atmosphere. The reaction mixture was stirred for 10 minutes at room temperature then ammonium carbonate (0.263 g, 2.859 mmol) was added and the resulting suspension was stirred at room temperature for 18 hours. The reaction volatiles were evaporated in vacuo and the resulting residue was diluted with ethyl acetate (15 mL) and water (10 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×15 mL). The combined organic extracts were washed with water, brine, dried (magnesium sulfate) and concentrated in vacuo to give a yellow foam which was purified by flash column chromatography on silica gel (55-85% ethyl acetate/petroleum ether) to give the title compound (I8) (0.276 g, 87%) as a yellow foam; 1H NMR (300 MHz, CDCl3) δ 1.48 (d, 9 H, J=1.1 Hz), 3.09 (d, 8 H, J=3.9 Hz), 3.58 (brs, 4 H), 3.66 (s, 2 H), 3.88 (d, 3 H, J=1.0 Hz), 5.48 (brs, 1 H), 5.78 (brs, 1 H), 6.54 (d, 1 H, J=1.3 Hz), 6.57 (s, 1 H), 7.23-7.25 (brs, 4 H), 7.72 (s, 1 H), 8.13 (d, 1 H, J=8.6 Hz) and 8.48 (s, 1 H). LCMS Method B: rt 8.52 min; m/z 615.4 [M+H]+.

Aufarbeitung

  1. stirringthe resulting suspension was stirred at room temperature for 18 hours
  2. customThe reaction volatiles
  3. customwere evaporated in vacuo
  4. additionthe resulting residue was diluted with ethyl acetate (15 mL) and water (10 mL)
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with ethyl acetate (2×15 mL)
  7. washThe combined organic extracts were washed with water, brine
  8. dry with materialdried (magnesium sulfate)
  9. concentrationconcentrated in vacuo
  10. customto give a yellow foam which
  11. customwas purified by flash column chromatography on silica gel (55-85% ethyl acetate/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-838185beb148456583fb3acdc450432c
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09120761B2

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