O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 22052368, compound

HRID 1831763Notes

Reaction equation

HRID 1831763 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([OH:17])=O.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[N:43]1([C:51]2[CH:56]=[CH:55][N:54]=[CH:53][CH:52]=2)[CH2:48][CH2:47][CH:46]([CH2:49][NH2:50])[CH2:45][CH2:44]1>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([NH:50][CH2:49][CH:46]1[CH2:45][CH2:44][N:43]([C:51]2[CH:56]=[CH:55][N:54]=[CH:53][CH:52]=2)[CH2:48][CH2:47]1)=[O:17]

Participants

5

Reactant 3

HCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 10607746[1-(Pyridin-4-yl)piperidin-4-yl]methanamineHCID 22052318HCID 22052318, compound

Product 1

HCID 22052368HCID 22052368, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.100 g (0.321 mmol) of 3-[2-(2,4-Dichlorophenyl)-ethoxy]-benzoic acid was dissolved in 2 ml of DMF and treated with 0.148 g (1.28 mmol) of N-NEM and 0.105 g (0.321 mmol) of TOTU and 0.123 g (0.64 mmol) of C-(3,4,5,6-Tetrahydro-2H-[1,4′]bipyridinyl-4-yl)-methylamine. The solution was stirred for 16 h at RT. The solvent was removed under reduced pressure, the residue was taken-up in ethyl acetate and the solution was washed twice with saturated aqueous sodium bicarbonate and once with saturated aqueous sodium chloride. The organic phase was dried with magnesium sulphate, filtered and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel eluting with a gradient of 0 to 17% MeOH in DCM.

Workup

  1. customThe solvent was removed under reduced pressure
  2. washthe solution was washed twice with saturated aqueous sodium bicarbonate and once with saturated aqueous sodium chloride
  3. dry with materialThe organic phase was dried with magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was chromatographed on silica gel eluting with a gradient of 0 to 17% MeOH in DCM

Sources & evidence

ORD record
ord-51bb9580254b461d8bb50ce705ed85de
Source dataset
uspto-grants-2006_06
Patent number
US07067665B2

Reaction notes

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