Diisopropylethylamine → HCID 86755171, compound

HRID 1979183Notes

Reaction equation

HRID 1979183 reaction equation
O.ON1C2C=CC=CC=2N=N1.Cl.[CH3:13][N:14]([CH3:23])[CH2:15][CH2:16][CH2:17][N:18]=[C:19]=[N:20][CH2:21][CH3:22].[CH:24]([N:27]([CH2:31][CH3:32])[CH:28]([CH3:30])[CH3:29])([CH3:26])[CH3:25]>C(Cl)Cl>[CH3:22][CH2:21][N:20]=[C:19]=[N:18][CH2:17][CH2:16][CH2:15][N:14]([CH3:23])[CH3:13].[CH3:32][CH2:31][N:27]([CH:28]([CH3:30])[CH3:29])[CH:24]([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 86755171HCID 86755171, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of acid (1.1 eq.) and 1-Hydroxybenzotriazole hydrate (HOBT; 1.1 eq.) in dry CH2Cl in an ice-bath under N2 was added 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI; 1.1 eq.). The mixture was stirred for 30 minutes. A solution of the amine (1.0 eq.) in dry methylene chloride was added drop-wise followed by N,N-Diisopropylethyamine (DIPEA; 1.5 eq.). The solution was allowed to stir at room temperature overnight. The reaction was quenched with sat. sodium bicarbonate and separated from methylene chloride. The organic layer was dried (Na2SO4), filtered through Celite, and evaporated. The crude product was chromatographed and converted to the HCl salt.

Workup

  1. stirringto stir at room temperature overnight
  2. customThe reaction was quenched with sat. sodium bicarbonate
  3. customseparated from methylene chloride
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered through Celite
  6. customevaporated
  7. customThe crude product was chromatographed

Sources & evidence

ORD record
ord-7593fa69b69a40ee97bacf12318e488c
Source dataset
uspto-grants-2001_05
Patent number
US06239154B1

Reaction notes

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