N-BOC-ethylenediamine → HCID 57500598, compound

HRID 1393693Notes

Reaction equation

HRID 1393693 reaction equation
OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.[CH3:23][N:24]1[C:28]2=[N:29][CH:30]=[C:31]([C:33]([OH:35])=O)[CH:32]=[C:27]2[C:26]([CH3:36])=[N:25]1.[NH2:37][CH2:38][CH2:39][NH:40][C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44]>CN(C)C=O>[CH3:23][N:24]1[C:28]2=[N:29][CH:30]=[C:31]([C:33]([NH:37][CH2:38][CH2:39][NH:40][C:41](=[O:47])[O:42][C:43]([CH3:45])([CH3:44])[CH3:46])=[O:35])[CH:32]=[C:27]2[C:26]([CH3:36])=[N:25]1

Participants

6

Reactant 4

HCID 187201N-BOC-ethylenediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 162278641,3-DIMETHYL-1H-PYRAZOLO[3,4-B]PYRIDINE-5-CARBOXYLIC ACIDHCID 178418300HCID 178418300, compound

Product 1

HCID 57500598HCID 57500598, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Hydroxybenzotriazole (3.55 g) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (4.45 g) were added to a solution of 1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid (4.00 g) in N,N-dimethylformamide (40 ml) with ice cooling. The mixture was stirred for 30 minutes at room temperature, and then t-butyl (2-aminoethyl)carbamate (3.65 ml) was added thereto and stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and ethyl acetate and water were added to the residue. The organic phase was washed with 10% citric acid solution, 4% sodium bicarbonate solution and a saturated saline solution. The product was dried under sodium sulfate anhydrous and concentrated under reduced pressure to give t-butyl {2-[(1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbonyl)amino]ethyl}carbamate (4.02 g, Y.:57%) as colorless crystals.

Workup

  1. stirringstirred overnight at room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate and water
  3. additionwere added to the residue
  4. washThe organic phase was washed with 10% citric acid solution, 4% sodium bicarbonate solution
  5. customThe product was dried under sodium sulfate anhydrous
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1d14d393644048548509a3843ec8ece9
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

Loading…