1-Pyrrolidineethanamine → HCID 24771537, compound

HRID 1670692Notes

Reaction equation

HRID 1670692 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[C:54]1[CH:55]=[CH:56][C:57]2[N:79]([CH:80]=1)[C:60]1[N:61]([C:70]3[CH:75]=[CH:74][C:73]([N+:76]([O-:78])=[O:77])=[CH:72][CH:71]=3)[C:62](=[O:69])[C:63]3[C:68]([C:59]=1[N:58]=2)=[CH:67][CH:66]=[CH:65][CH:64]=3.[N:81]1([CH2:86][CH2:87][NH2:88])[CH2:85][CH2:84][CH2:83][CH2:82]1>O1CCOCC1>[N+:76]([C:73]1[CH:72]=[CH:71][C:70]([N:61]2[C:60]3[N:79]4[CH:80]=[C:54]([NH:88][CH2:87][CH2:86][N:81]5[CH2:85][CH2:84][CH2:83][CH2:82]5)[CH:55]=[CH:56][C:57]4=[N:58][C:59]=3[C:68]3[C:63](=[CH:64][CH:65]=[CH:66][CH:67]=3)[C:62]2=[O:69])=[CH:75][CH:74]=1)([O-:78])=[O:77]

Participants

6

Reactant 4

HCID 13441-PyrrolidineethanamineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 57767011HCID 57767011, compound

Product 1

HCID 24771537HCID 24771537, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

An oven-dried pyrex screw-tube was charged with rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl ((rac)-BINAP) (0.3 equiv., 0.138 mmol, 0.086 g), Pd2(dibenzylidene-acetone)3 (Pd2 dba3) (0.1 equiv., 0.046 mmol, 0.042 g) and Cs2CO3 (1.4 equiv., 0.643 mmol, 0.210 g). Dry dioxane (1 ml) was added and the screw-tube was purged with Ar. The reaction mixture was heated at 80° C. for 30 min, after which it was allowed to cool to room temperature. 9-Bromo-6-(4-nitrophenyl)-pyrido[2′,1′:2,3]-imidazo[4,5-c]isoquinolin-5(6H)-one (18) (1.0 equiv., 0.460 mmol, 0.200 g) and pyrrolidineethanamine (1.0 equiv., 0.460 mmol, 0.052 g) were added and the reaction mixture was stirred at 100° C. until no starting materials were left. The progress of the reaction was monitored by LCMS. Removal of the solvent under reduced pressure, followed by column chromatography (gradient elution: dichloromethane→dichloromethane/methanol 9:1) of the resulting residue gave 6-(4-nitrophenyl)-9-(2-pyrrolidin-1-yl-ethylamino)-pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one (67) (0.055 g, yield=26%, purity (LC)=97%).

Workup

  1. customthe screw-tube was purged with Ar
  2. temperatureto cool to room temperature
  3. waitwere left
  4. customRemoval of the solvent under reduced pressure
  5. washfollowed by column chromatography (gradient elution: dichloromethane→dichloromethane/methanol 9:1) of the resulting residue

Sources & evidence

ORD record
ord-46e85f0545ca464dab9492583be5567d
Source dataset
uspto-grants-2011_08
Patent number
US07994187B2

Reaction notes

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