Triethylamine → HCID 178425365, Verbindung

HRID 642822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 642822
[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@@H:18]([C:30]([OH:32])=O)[CH2:19][C:20]3[CH:28]=[C:27]([CH3:29])[C:23]4[NH:24][CH:25]=[N:26][C:22]=4[CH:21]=3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:33]=[CH:34][CH:35]=[CH:36][C:4]=2[NH:3]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.[CH2:66]([N:73]1[CH2:78][CH2:77][CH:76]([CH:79]2[CH2:84][CH2:83][NH:82][CH2:81][CH2:80]2)[CH2:75][CH2:74]1)[C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.CN(C=O)C>[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@H:18]([CH2:19][C:20]3[CH:28]=[C:27]([CH3:29])[C:23]4[NH:24][CH:25]=[N:26][C:22]=4[CH:21]=3)[C:30]([N:82]3[CH2:81][CH2:80][CH:79]([CH:76]4[CH2:75][CH2:74][N:73]([CH2:66][C:67]5[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=5)[CH2:78][CH2:77]4)[CH2:84][CH2:83]3)=[O:32])=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:33]=[CH:34][CH:35]=[CH:36][C:4]=2[NH:3]1

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 337006491-Benzyl-4,4'-bipiperidineHCID 178425374(R)-1-carboxy-2-(7-methyl-1H-benzimidazol-5-yl)-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Produkt 1

HCID 178425365HCID 178425365, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 120 mg (0.22 mmol) (R)-1-carboxy-2-(7-methyl-1H-benzimidazol-5-yl)-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate, 85 mg (0.27 mmol) TBTU and 50 μL (0.36 mmol) triethylamine in 10 mL THF and 1 mL DMF was stirred for 1 h at RT, then combined with 80 mg (0.31 mmol) 1-benzyl-[4,4′]bipiperidinyl and stirred overnight at RT. The reaction solution was combined with 1 mL saturated Na2CO3 solution and extracted with 100 mL EtOAc. The organic phase was dried over Na2SO4, filtered and evaporated down i.vac. The residue was purified via HPLC, the fractions containing the product were combined and evaporated to dryness i.vac.

Aufarbeitung

  1. extractionextracted with 100 mL EtOAc
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated down i.vac
  5. customThe residue was purified via HPLC
  6. additionthe fractions containing the product
  7. customevaporated to dryness i.vac

Quellen und Nachweise

ORD-Eintrag
ord-29b124558d3344ab904bfd3ea344d175
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696195B2

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