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

HRID 38117

Reaction equation

HRID 38117 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-c32a277b93bd4a4fa6a6d77eca32ddec
Source dataset
uspto-grants-2013_09
Patent number
US08524717B2

Linked notes

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