Triethylamine → HCID 21273498, compound

HRID 1382930Notes

Reaction equation

HRID 1382930 reaction equation
ClC(OCC(C)C)=O.[C:9]1([C:15]2[N:16]=[C:17]([CH2:26][CH2:27][C:28]([OH:30])=O)[NH:18][C:19]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:31]([N:33](CC)CC)C.Cl.CN.N12CCCN=C1CCCCC2>CN(C)C=O.O>[CH3:31][NH:33][C:28](=[O:30])[CH2:27][CH2:26][C:17]1[NH:16][C:15]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[C:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:18]=1

Participants

8

Reactant 5

HCID 8471Triethylamine2×HCID 62365Isobutyl chloroformateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 30431821H-Imidazole-2-propanoic acid, 4,5-diphenyl-HCID 6364545Methylamine hydrochloride

Product 1

HCID 21273498HCID 21273498, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

3.2 ml (0.024 mol) of isobutyl chloroformate are added dropwise at -5° to a solution of 7.0 g (0.024 mol) of 4,5-diphenylimidazole-2-propionic acid and 3.36 ml (0.024 mol) of triethylamine in 80 ml of dimethylformamide. After stirring at 0°-5° for 30 minutes 1.64 g (0.024 mol) of methylamine hydrochloride and 3.36 ml (0.024 mol) of triethylamine in 32 ml of dimethylformamide and 1.65 ml of water are added. The temperature is then left to rise to room temperature and the mixture is stirred for a further 20 hours. After concentration under reduced pressure the residue is boiled up in 250 ml of methanol and treated with 3.6 ml (0.024 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), whereby a clear solution results. 4.8 g of N-methyl-4.5-diphenylimidazole-2-propionamide, m.p. 195°-200° (dec.), result by cooling in an ice-bath. From the mother liquor there are obtained by concentration and treatment with water a further 2 g of the same product, m.p. 195°-200°. Total yield: 6.8 g (93%).

Workup

  1. additionare added
  2. waitThe temperature is then left
  3. customto rise to room temperature
  4. concentrationAfter concentration under reduced pressure the residue
  5. customresults

Sources & evidence

ORD record
ord-0f454b1c078c44f489bf330a73f1f2fd
Source dataset
uspto-grants-1989_02
Patent number
US04808605

Reaction notes

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