Acetic acid;iodosylbenzene → tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(3-(7-(2-methoxyethoxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate

HRID 339052Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 339052
[CH3:1][C@:2]1([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:6][CH2:5][N:4]([C@@H:7]([C:12]2[CH:13]=[N:14][C:15]([NH:18][NH2:19])=[CH:16][CH:17]=2)[C:8]([F:11])([F:10])[F:9])[CH2:3]1.[CH3:28][O:29][CH2:30][CH2:31][O:32][C:33]1[CH:42]=[C:41]2[C:36]([CH:37]=[CH:38][C:39]([CH:43]=O)=[N:40]2)=[CH:35][CH:34]=1.C(O)(=O)C.C(O)(=O)C.I(C1C=CC=CC=1)=O>CCO>[CH3:1][C@:2]1([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:6][CH2:5][N:4]([C@@H:7]([C:12]2[CH:17]=[CH:16][C:15]3[N:14]([C:43]([C:39]4[CH:38]=[CH:37][C:36]5[C:41](=[CH:42][C:33]([O:32][CH2:31][CH2:30][O:29][CH3:28])=[CH:34][CH:35]=5)[N:40]=4)=[N:19][N:18]=3)[CH:13]=2)[C:8]([F:9])([F:10])[F:11])[CH2:3]1

Komponenten

5

Edukt 3

HCID 73357407Acetic acid;iodosylbenzeneHCID 86707435tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamateHCID 867074817-(2-Methoxyethoxy)quinoline-2-carbaldehyde

Produkt 1

HCID 86707539tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(3-(7-(2-methoxyethoxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamateAusbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (53 mg, 0.14 mmol), 7-(2-methoxyethoxy)quinoline-2-carbaldehyde (30 mg, 0.13 mmol) and EtOH (1.4 mL) was stirred at ambient temperature overnight. The solvent was removed under reduced pressure. The residue was dissolved in DCM (1.4 mL) and iodosobenzene diacetate (54 mg, 0.17 mmol) was added. The reaction mixture was stirred at ambient temperature overnight and then loaded to a silica gel column eluting with 1:2 to 3:1 EtOAc/hexanes to give tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(3-(7-(2-methoxyethoxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate (72 mg, 92%).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in DCM (1.4 mL)
  3. stirringThe reaction mixture was stirred at ambient temperature overnight
  4. washeluting with 1:2 to 3:1 EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-4db7f348cb9749128fca467ce4829f63
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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