1-Piperazinecarboxylic acid, ethyl ester → HCID 68534100, compound

HRID 1992491Notes

Reaction equation

HRID 1992491 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([CH:26]([CH3:28])[CH3:27])[C:21]([C:29]([OH:31])=O)=[CH:20]3)=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:32]([O:34][C:35]([N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)=[O:36])[CH3:33].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([CH:26]([CH3:27])[CH3:28])[C:21]([C:29]([N:40]2[CH2:39][CH2:38][N:37]([C:35]([O:34][CH2:32][CH3:33])=[O:36])[CH2:42][CH2:41]2)=[O:31])=[CH:20]3)=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 685382125-(4-tert-butoxycarbonyl-[1,4]diazepane-1-carbonyl)-1-isopropyl-1H-indole-2-carboxylic acid

Product 1

HCID 68534100HCID 68534100, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 5-(4-tert-butoxycarbonyl-[1,4]diazepane-1-carbonyl)-1-isopropyl-1H-indole-2-carboxylic acid (144 mg) and 4-ethoxy carbonyl piperazine (1 eq., 53 mg) in acetonitrile (5 ml) was added N-hydroxybenzotriazole (0.2 eq., 9 mg). The mixture was stirred 5 min before the addition of N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide hydrochloride (1.1 eq., 77 mg). The mixture was stirred two days at room temperature. The mixture was evaporated under reduced pressure and the residue purified by column chromatography on silica gel (19:1 EtOAc/MeOH) to afford the product as an off-white powder (195 mg, 89%). MS (m/z): 570.3 (M+H)+.

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customthe residue purified by column chromatography on silica gel (19:1 EtOAc/MeOH)

Sources & evidence

ORD record
ord-53fa5dde2b854e5a8e998ef9c056efaf
Source dataset
uspto-grants-2010_01
Patent number
US07648979B2

Reaction notes

Loading…