Sodium hydride → Tert-butyl (trans)-2-(1,1'-biphenyl-4-yl)cyclopropyl(2-(4-methylpiperazin-1-yl)-2-oxoethyl)carbamate

HRID 38117

Reaktionsgleichung

Reaktionsgleichung von HRID 38117
[H-].[Na+].[C:3]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:11][C@H:10]2[NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:5][CH:4]=1.Cl[CH2:27][C:28]([N:30]1[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]1)=[O:29]>CN(C=O)C>[C:3]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:11][C@H:10]2[N:12]([CH2:27][C:28]([N:30]2[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]2)=[O:29])[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 8181732-Chloro-1-(4-methylpiperazin-1-yl)ethanoneHCID 86658778Tert-butyl(trans)-2-(1,1'-biphenyl-4-yl)cyclopropylcarbamate

Produkt 1

HCID 67448639Tert-butyl (trans)-2-(1,1'-biphenyl-4-yl)cyclopropyl(2-(4-methylpiperazin-1-yl)-2-oxoethyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

To a suspension of 1.5 equiv of NaH in dry DMF (10 vols) at 0° C. was added a solution of tert-butyl(trans)-2-(1,1′-biphenyl-4-yl)cyclopropylcarbamate derivative (1 equiv) in dry DMF (2 vols) and stirr for 30 mins. Then, added a solution of 1-(chloroacetyl)-4-methylpiperazine (1.5 equiv) in dry DMF (10 mL) at 0° C., stirred for 1 h at 0° C. to RT. The progress of the reaction was monitored by TLC. After completion, reaction mixture was poured into ice water and extracted with EtOAC. The combined extracts were washed with water, brine, dried over anhydrous Na2SO4, filtered and evaporated. The crude residue was purifying by preparative HPLC to get tert-butyl (trans)-2-(1,1′-biphenyl-4-yl)cyclopropyl(2-(4-methylpiperazin-1-yl)-2-oxoethyl)carbamate derivative

Aufarbeitung

  1. customAfter completion, reaction mixture
  2. extractionextracted with EtOAC
  3. washThe combined extracts were washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude residue was purifying by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-c32a277b93bd4a4fa6a6d77eca32ddec
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524717B2

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