2-Methyl-1,3-thiazole-4-carboxylic acid → 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

HRID 890682Notes

Reaction equation

HRID 890682 reaction equation
Cl.[CH3:2][N:3]([CH3:12])[CH2:4][CH2:5][CH2:6][N:7]=[C:8]=[N:9][CH2:10][CH3:11].CC1SC=C(C(O)=O)N=1>C(Cl)Cl>[CH3:11][CH2:10][N:9]=[C:8]=[N:7][CH2:6][CH2:5][CH2:4][N:3]([CH3:12])[CH3:2]

Participants

4

Reactant 2

HCID 2847282-Methyl-1,3-thiazole-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (42.3 mg, 0.214 mmol) in dry CH2Cl2 (1 mL) was added 2-methyl-1,3-thiazole-4-carboxylic acid (30.7 mg, 0.214 mmol) at room temperature under a nitrogen atmosphere. The resulting bright red mixture was allowed to stir for 1 hour, then Intermediate 51 (75 mg, 0.204 mmol) was added in one portion. After stirring at room temperature overnight, the reaction was concentrated at reduced pressure and the residue purified via radial chromatography (1 mm plate with 3% MeOH in CH2Cl2) to provide Example 27 as a clear film (21 mg, 20%).

Workup

  1. stirringAfter stirring at room temperature overnight
  2. concentrationthe reaction was concentrated at reduced pressure
  3. customthe residue purified via radial chromatography (1 mm plate with 3% MeOH in CH2Cl2)
  4. customto provide Example 27 as a clear film (21 mg, 20%)

Sources & evidence

ORD record
ord-8c7532ad40a24419bf3b63066a5ef4f4
Source dataset
uspto-grants-2006_02
Patent number
US06998416B2

Reaction notes

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