Triethylamine → (S)-4-(4-(2-(pyrrolidin-2-yl)acetyl)piperazin-1-yl)-9H-diprido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 60266

Reaktionsgleichung

Reaktionsgleichung von HRID 60266
[N:1]1([C:7]2[C:15]3[C:14]4[CH:16]=[C:17]([C:20]#[N:21])[N:18]=[CH:19][C:13]=4[N:12](COCC[Si](C)(C)C)[C:11]=3[N:10]=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(OC([N:37]1[CH2:41][CH2:40][CH2:39][C@H:38]1[CH2:42][C:43](O)=[O:44])=O)(C)(C)C.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>C(Cl)Cl>[NH:37]1[CH2:41][CH2:40][CH2:39][C@H:38]1[CH2:42][C:43]([N:4]1[CH2:3][CH2:2][N:1]([C:7]2[C:15]3[C:14]4[CH:16]=[C:17]([C:20]#[N:21])[N:18]=[CH:19][C:13]=4[NH:12][C:11]=3[N:10]=[CH:9][CH:8]=2)[CH2:6][CH2:5]1)=[O:44]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 688605(S)-2-(1-BOC-2-pyrrolidinyl)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 672574164-(piperazin-1-yl)-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

Produkt 1

HCID 53250548(S)-4-(4-(2-(pyrrolidin-2-yl)acetyl)piperazin-1-yl)-9H-diprido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of 4-(piperazin-1-yl)-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (100 mg, 0.2 mmol), (S)-2-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)acetic acid (220 mg, 1.0 mmol), 1-hydroxybenzotriazole (50 mg, 0.4 mmol), (3-dimethylamino-propyl)-ethyl-carbodiimide hydrogen chloride (70 mg, 0.4 mmol), and triethylamine (0.1 mL, 0.7 mmol) in methylene chloride (2.5 mL) was stirred at ambient temperature overnight. The reaction mixture was diluted with methylene chloride (50 mL) and washed with saturated aqueous sodium bicarbonate solution (20 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified flash chromatography (silica, 4 g, ISCO, 0-70% ethyl acetate in heptane) to afford the title compound as a white foam, which was used in the next step without any further purification (140 mg).

Aufarbeitung

  1. washwashed with saturated aqueous sodium bicarbonate solution (20 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified flash chromatography (silica, 4 g, ISCO, 0-70% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-b31be6760dfb40c4b15d92d1ee43ef56
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440976B2

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