2-Bromopropane → HCID 68876850, compound

HRID 1454235Notes

Reaction equation

HRID 1454235 reaction equation
[C:1]([O:5][C:6](=[O:33])[N:7]([CH2:9][C:10]1[CH:15]=[C:14]([CH2:16][N:17]2[CH2:22][CH2:21][NH:20][C:19](=[O:23])[CH2:18]2)[CH:13]=[CH:12][C:11]=1[O:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH:37]([CH3:39])[CH3:38]>CN(C=O)C>[C:1]([O:5][C:6](=[O:33])[N:7]([CH2:9][C:10]1[CH:15]=[C:14]([CH2:16][N:17]2[CH2:22][CH2:21][N:20]([CH:37]([CH3:39])[CH3:38])[C:19](=[O:23])[CH2:18]2)[CH:13]=[CH:12][C:11]=1[O:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 68848904HCID 68848904, compound

Product 1

HCID 68876850HCID 68876850, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of [2-(3,4-dichloro-phenoxy)-5-(3-oxo-piperazin-1-ylmethyl)-benzyl]-methyl-carbamic acid tert-butyl ester 79 mg, 0.16 mmol) in DMF (3.2 mL) at 0° C. was added NaH (90%, 7.6 mg). After 30 min, 2-bromopropane (15 μL, 0.16 mmol) was added and the reaction was allowed to come to rt and stir overnight. The mixture was quenched with satd. aq. NaHCO3 and extracted with DCM. The combined organic layers were dried (Na2SO4) and concentrated. The crude product was purified by FCC to provide the title compound (35 mg, 41%). MS (ESI): mass calcd. for C27H35Cl2N3O4, 535.20; m/z found, 536.2 [M+H].

Workup

  1. customto come to rt
  2. customThe mixture was quenched with satd
  3. extractionaq. NaHCO3 and extracted with DCM
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by FCC

Sources & evidence

ORD record
ord-cd50486bd9844bdbb20c8d51f23692ff
Source dataset
uspto-grants-2009_01
Patent number
US07479493B2

Reaction notes

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