Diisopropylethylamine → 1-Methyl-piperidine-4-carboxylic acid [2-(2-methoxy-benzylamino)-quinolin-6-yl]-amide

HRID 1803078

Reaktionsgleichung

Reaktionsgleichung von HRID 1803078
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][CH:6]([C:9]([OH:11])=O)[CH2:5][CH2:4]1.C(N(C(C)C)C(C)C)C.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH3:55][O:56][C:57]1[CH:75]=[CH:74][CH:73]=[CH:72][C:58]=1[CH2:59][NH:60][C:61]1[CH:70]=[CH:69][C:68]2[C:63](=[CH:64][CH:65]=[C:66]([NH2:71])[CH:67]=2)[N:62]=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:55][O:56][C:57]1[CH:75]=[CH:74][CH:73]=[CH:72][C:58]=1[CH2:59][NH:60][C:61]1[CH:70]=[CH:69][C:68]2[C:63](=[CH:64][CH:65]=[C:66]([NH:71][C:9]([CH:6]3[CH2:5][CH2:4][N:3]([CH3:2])[CH2:8][CH2:7]3)=[O:11])[CH:67]=2)[N:62]=1

Komponenten

8

Edukt 6

HCID 81531Diisopropylethylamine2×HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27600434-Piperidinecarboxylic acid, 1-methyl-, hydrochloride (1:1)HCID 43450845N2-(2-Methoxy-benzyl)-quinoline-2,6-diamine

Produkt 1

HCID 866344211-Methyl-piperidine-4-carboxylic acid [2-(2-methoxy-benzylamino)-quinolin-6-yl]-amideAusbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-methyl-piperidine-4-carboxylic acid hydrochloride salt (35 mg, 179 mmol) in tetrahydrofurane (3 ml) were added at room temperature N-ethyldiisopropylamine (74 mg, 0.573 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (27 mg, 0.197 mmol), N,N-diisopropyl ethyl amine (74 mg, 0.197 mmol) and 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride (38 mg, 0.197 mmol) and the mixture was allowed to stir for 90 min. N2-(2-Methoxy-benzyl)-quinoline-2,6-diamine (example 10, step B, 50 mg, 0.179 mmol) was added and the reaction mixture was allowed to stir for 17 h, poured into sat. sodium bicarbonate solution (30 ml) and extracted with dichloromethane (2×30 ml). The combined organic layers were washed with water (30 ml), dried (MgSO4) and evaporated. The crude product was further purified by flash chromatography on silica gel (heptane/ethyl acetate) and crystallization (ethyl acetate/heptane) to yield the title compound as white solid (35 mg, 48%). MS: m/e=405.5 (M+H+).

Aufarbeitung

  1. stirringto stir for 17 h
  2. extractionextracted with dichloromethane (2×30 ml)
  3. washThe combined organic layers were washed with water (30 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude product was further purified by flash chromatography on silica gel (heptane/ethyl acetate) and crystallization (ethyl acetate/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-4d48e4bd7fbe4e64b5a0cbe33b7701ed
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08350028B2

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