Water → HCID 67123533, compound

HRID 1887017Notes

Reaction equation

HRID 1887017 reaction equation
C1C=CC2N([OH:10])N=NC=2C=1.O.CCN=C=NC[CH2:18][CH2:19][N:20]([CH3:22])[CH3:21].Cl.Cl.[O:25]=[C:26]1[NH:34][C:33]2[C:28](=[N:29][C:30]([C:35]3[CH:36]=[N:37][N:38]4[CH:43]=[CH:42][C:41]([C:44]#[N:45])=[CH:40][C:39]=34)=[N:31][CH:32]=2)[N:27]1[C@H:46]1[CH2:51][CH2:50][CH2:49][NH:48][CH2:47]1>CN(C=O)C>[CH3:21][N:20]([CH3:22])[CH2:19][C:18]([N:48]1[CH2:49][CH2:50][CH2:51][C@H:46]([N:27]2[C:26](=[O:25])[NH:34][C:33]3[C:28]2=[N:29][C:30]([C:35]2[CH:36]=[N:37][N:38]4[CH:43]=[CH:42][C:41]([C:44]#[N:45])=[CH:40][C:39]=24)=[N:31][CH:32]=3)[CH2:47]1)=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67123442HCID 67123442, compound

Product 1

HCID 67123533HCID 67123533, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N,N-dimethylglicine (10 mg, 0.095 mmol) in anhydrous DMF (2 mL). HOBt.H2O was added. After 15 min, EDC.HCl (24 mg, 0.126 mmol) and the compound obtained in example 6 (31 mg, 0.063 mmol) were added. The reaction mixture was stirred at room temperature for 2.5 h and the solvent was concentrated off. It was quenched with saturated NaHCO3 aqueous solution (15 mL) and extracted with EtOAc (3×15 mL). The combined organic phases were dried over anhydrous Mg2SO4, filtered and concentrated. The crude residue was chromatographed on a silica gel flash system (ISCO Rf) using hexanes/acetone mixtures of increasing polarity as eluent to afford 8.2 mg of the titled compound (29% yield).

Workup

  1. concentrationthe solvent was concentrated off
  2. customIt was quenched with saturated NaHCO3 aqueous solution (15 mL)
  3. extractionextracted with EtOAc (3×15 mL)
  4. dry with materialThe combined organic phases were dried over anhydrous Mg2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was chromatographed on a silica gel flash system (ISCO Rf)
  8. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-fabb18d2d0214c7c8ef9b0e925831991
Source dataset
uspto-grants-2013_08
Patent number
US08501735B2

Reaction notes

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