Sodium hydride → HCID 67369469, compound

HRID 38115

Reaction equation

HRID 38115 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C@@H:17]2[CH2:19][C@H:18]2[NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[CH2:29][C:30]([N:32]1[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]1)=[O:31]>CN(C=O)C>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C@@H:17]2[CH2:19][C@H:18]2[N:20]([CH2:29][C:30]([N:32]2[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]2)=[O:31])[C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[CH:13][CH:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 8181732-Chloro-1-(4-methylpiperazin-1-yl)ethanoneHCID 15480693tert-Butyl(trans)-2-[4-(benzyloxy)phenyl]cyclopropylcarbamate2×

Product 1

HCID 67369469HCID 67369469, compound

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 ter-butyl(trans)-2-[4-(benzyloxy)phenyl]cyclopropylcarbamate (Intermediate C, 1 equiv) in dry DMF (2 vols) and stirr for 30 mins. Then, added was 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-[4(benzyloxy)phenyl]cyclopropyl(2-(4-methylpiperazin-1-yl)-2-oxoethyl)carbamate derivative.

Workup

  1. additionThen, added
  2. customat 0° C.
  3. customAfter completion, reaction mixture
  4. extractionextracted with EtOAC
  5. washThe combined extracts were washed with water, brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude residue was purifying by preparative HPLC

Sources & evidence

ORD record
ord-56d03ec35a2d4023a0d8ce3fad2c7d94
Source dataset
uspto-grants-2013_09
Patent number
US08524717B2

Linked notes

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