Dimethylformamide → HCID 86759567, compound

HRID 2416639Notes

Reaction equation

HRID 2416639 reaction equation
[C:1]([O:5]C(NCC(O)=O)=O)([CH3:4])([CH3:3])[CH3:2].Cl.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26]CNC[CH2:22]2)=[CH:17][CH:16]=1.Cl.[CH2:28]([N:30]=[C:31]=NCCCN(C)C)C.[OH:39]N1C2C=CC=CC=2N=N1.[CH3:49][N:50]([CH3:53])[CH:51]=[O:52]>C(N(CC)CC)C>[C:1]([O:5][N:30]([CH2:31][C:51]([N:50]1[CH2:53][CH2:22][N:21]([C:18]2[CH:17]=[CH:16][C:15]([Cl:14])=[CH:20][CH:19]=2)[CH2:26][CH2:49]1)=[O:52])[CH:28]=[O:39])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 30847201-(4-Chlorophenyl)piperazine Hydrochloride

Product 1

HCID 86759567HCID 86759567, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a suspension of 2-(tert-butoxycarbonylamino)acetic acid (16.3 g) and 1-(4-chlorophenyl)piperazine hydrochloride (21.7 g) in N,N-dimethylformamide (200 ml) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (19.6 g) and N-hydroxybenzotriazole (13.8 g) at 0° C. To this suspension was added dropwise triethylamine (10.4 g). The mixture was stirred at room temperature for 20 hours. The reaction mixture was poured into ice-cold water and the resulting solid was collected by filtration. The solid was washed successively with saturated aqueous sodium hydrogencarbonate solution and water. The solid was dried to give the title compound (29 g).

Workup

  1. additionThe reaction mixture was poured into ice-cold water
  2. filtrationthe resulting solid was collected by filtration
  3. washThe solid was washed successively with saturated aqueous sodium hydrogencarbonate solution and water
  4. customThe solid was dried

Sources & evidence

ORD record
ord-1cff4fbf807a458b83b1abde1e440503
Source dataset
uspto-grants-2004_11
Patent number
US06825200B1

Reaction notes

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