Anthranilic Acid → HCID 131726013, compound

HRID 1246961Notes

Reaction equation

HRID 1246961 reaction equation
[C:1]([OH:10])(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2([C:22]#[N:23])[CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:13]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>ClCCl>[NH2:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2([C:22]#[N:23])[CH2:21][CH2:20][CH2:19]2)=[CH:16][CH:17]=1)=[O:10]

Participants

6

Reactant 4

HCID 227Anthranilic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 21906962HCID 21906962, compound

Product 1

HCID 131726013HCID 131726013, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of anthranilic acid (1.4 g) and 1-(4-aminophenyl)cyclobutane-carbonitrile (1 eq) and TEA (1.2 eq) in dichloromethane (80 ml) was stirred with EDCI (1.25 eq) and HOBt (1 eq) at RT overnight. The reaction was washed with sat. NaHCO3, H2O followed by brine, dried over Na2SO4 and evaporated. The residue was purified by column chromatography to give (2-aminophenyl)-N-[4-(cyanocyclobutyl)phenyl]-carboxamide.

Workup

  1. washThe reaction was washed with sat. NaHCO3, H2O
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8a287090be5a45018a98dcd1707f9b18
Source dataset
uspto-grants-2006_10
Patent number
US07129252B2

Reaction notes

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