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Triethylamine → methyl (R)-3-methoxy-4-[1-methyl-5-(2-methyl-4,4,4-trifluorobutylcarbamoyl)indol-3-ylmethyl]benzoate

HRID 1741917
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1741917
Cl.[CH3:2][C@H:3]([CH2:6][C:7]([F:10])([F:9])[F:8])[CH2:4][NH2:5].[C:11]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH3:23])[CH:18]=[C:17]2[CH2:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][C:26]=1[O:35][CH3:36])(O)=[O:12].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:36][O:35][C:26]1[CH:27]=[C:28]([CH:33]=[CH:34][C:25]=1[CH2:24][C:17]1[C:16]2[C:20](=[CH:21][CH:22]=[C:14]([C:11](=[O:12])[NH:5][CH2:4][C@H:3]([CH3:2])[CH2:6][C:7]([F:10])([F:9])[F:8])[CH:15]=2)[N:19]([CH3:23])[CH:18]=1)[C:29]([O:31][CH3:32])=[O:30]
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Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9998178Methyl 4-(5-carboxy-1-methylindol-3-ylmethyl)-3-methoxybenzoateHCID 12004108(R)-2-methyl-4,4,4-trifluorobutylamine hydrochloride

Produkt 1

HCID 10050661methyl (R)-3-methoxy-4-[1-methyl-5-(2-methyl-4,4,4-trifluorobutylcarbamoyl)indol-3-ylmethyl]benzoate
Ausbeute 55,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of (R)-2-methyl-4,4,4-trifluorobutylamine hydrochloride (9.79 g), methyl 4-(5-carboxy-1-methylindol-3-ylmethyl)-3-methoxybenzoate (20.55 g), 4-dimethylaminopyridine (7.45 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (15.07 g) and triethylamine (9.3 mL) was dissolved in dry methylene chloride (240 mL) and the solution was stirred under an inert atmosphere for 18 h. The mixture was diluted with methylene chloride (200 mL) and washed twice with 1N hydrochloric acid. The combined acid washes were back extracted with methylene chloride and the combined organic extracts were washed (water, brine), dried (MgSO4), and evaporated. The residue was purified by flash chromatography, eluting with 97:3 methylene chloride:ethyl acetate to give methyl (R)-3-methoxy-4-[1-methyl-5-(2-methyl-4,4,4-trifluorobutylcarbamoyl)indol-3-ylmethyl]benzoate (14.48 g, 55%) as a white solid; mp 150°-151° C.; partial NMR (300 MHz, CDCl3): 1.12 (d, 3H, CH3), 1.98-2.08 (m, 1H, CHCH3) 2.12-2.44 (m, 2H, CF3CH2), 3.30-3.58 (m, 2H, CH2N), 3.76 (s, 3H, NCH3), 3.90 (s, 3H, OCH3), 3.93 (s, 3H, OCH3), 4.13 (s, 2H, ArCH2Ar'), 6.23 (br t, 1H, NHCO).

Aufarbeitung

  1. washwashed twice with 1N hydrochloric acid
  2. extractionThe combined acid washes were back extracted with methylene chloride
  3. washthe combined organic extracts were washed (water, brine)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by flash chromatography
  7. washeluting with 97:3 methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-22d6946b8f52498f89950627d2efde73
Quelldatensatz
uspto-grants-1994_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05334765

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