Potassium Carbonate → Tert-butyl benzyl[(3-{methyl[2-(methylamino)ethyl]amino}propyl)sulfonyl]carbamate

HRID 421974Notes

Reaction equation

HRID 421974 reaction equation
[CH2:1]([N:8]([S:16]([CH2:19][CH2:20][CH2:21]Cl)(=[O:18])=[O:17])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N:24]([CH3:28])[CH2:25][CH2:26][NH2:27].[C:29]([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:1]([N:8]([S:16]([CH2:19][CH2:20][CH2:21][N:27]([CH3:29])[CH2:26][CH2:25][NH:24][CH3:28])(=[O:18])=[O:17])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66053N,N-DimethylethylenediamineHCID 66674695Tert-butyl benzyl[(3-chloropropyl)sulfonyl]carbamate

Product 1

HCID 66674500Tert-butyl benzyl[(3-{methyl[2-(methylamino)ethyl]amino}propyl)sulfonyl]carbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

Tert-butyl benzyl[(3-chloropropyl)sulfonyl]carbamate was dissolved in MeCN (0.2 M) and N,N-dimethylethane-1,2-diamine (5 eq.) was added followed by K2CO3 (5 eq.). The mixture was stirred at 65° C. overnight. The solvent was removed under reduced pressure and the residual material was dissolved in EtOAc and washed with water. After drying over Na2SO4, all volatiles were evaporated in vacuo and the residual material used in the next step without purification. MS (ES+) m/z 400 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residual material was dissolved in EtOAc
  3. washwashed with water
  4. dry with materialAfter drying over Na2SO4
  5. customall volatiles were evaporated in vacuo
  6. customthe residual material used in the next step without purification

Sources & evidence

ORD record
ord-a7142f2d67834a489b564e3845830008
Source dataset
uspto-grants-2012_01
Patent number
US08101595B2

Reaction notes

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