Anthranilamide → 4-[1-(2-Carbamoylphenylcarbamoyl)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 238236Notes

Reaction equation

HRID 238236 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:16]([OH:18])=O)[CH3:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22]([NH2:24])=[O:23].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.CCN(CC)CC>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH:14]([C:16](=[O:18])[NH:19][C:20]2[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=2[C:22](=[O:23])[NH2:24])[CH3:15])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 6942AnthranilamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 177818912-[1-(Tert-butoxycarbonyl)piperidin-4-yl]propanoic acid

Product 1

HCID 599933244-[1-(2-Carbamoylphenylcarbamoyl)-ethyl]-piperidine-1-carboxylic acid tert-butyl esterYield 53.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A mixture of 4-(1-carboxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (28.6 g, 0.11 mol), 2-aminobenzamide (13.7 g, 0.1 mol), EDCI (21.3 g, 0.11 mol), HOBT (15 g, 0.11 mol) and Et3N (25 mL) in CH2Cl2 (500 mL) was stirred for 48 hr. The reaction mixture was diluted with CH2Cl2 (1000 mL) and washed with NaHCO3 (aq), the organic layer was dried with Na2SO4 and concentrated in vacuo to give the product a yellow solid (20 g, 48%) which was used directly for the next step.

Workup

  1. washwashed with NaHCO3 (aq)
  2. dry with materialthe organic layer was dried with Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4605a8e3df2948349118e090ad701c52
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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