3,4-Diaminobenzonitrile → HCID 69698598, compound

HRID 412615Notes

Reaction equation

HRID 412615 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH2:10])[C:5]#[N:6].[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([O:24][C:25]2[CH:35]=[CH:34][C:28]([O:29][CH2:30][C:31](O)=[O:32])=[CH:27][CH:26]=2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>O1CCCC1>[C:11]([O:15][C:16]([N:18]1[CH2:19][CH2:20][CH:21]([O:24][C:25]2[CH:35]=[CH:34][C:28]([O:29][CH2:30][C:31](=[O:32])[NH:1][C:2]3[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[CH:8][C:9]=3[NH2:10])=[CH:27][CH:26]=2)[CH2:22][CH2:23]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 7372853,4-DiaminobenzonitrileHCID 185363314-(1-Tert-butoxycarbonylpiperidin-4-yloxy)phenoxyacetic acid

Product 1

HCID 69698598HCID 69698598, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,4-diaminobenzonitrile (474 mg), 4-(1-tert-butoxycarbonylpiperidin-4-yloxy)phenoxyacetic acid (1.25 g) in tetrahydrofuran (50 ml) was added 1-ethoxycarbonyl-2-ethoxy-1,2-dihydroxyquinoline (1.06 g) with ice-cooling, and the mixture was stirred at room temperature for 16 hours. After completion of the reaction, the solvent was evaporated and to the obtained residue were added chloroform and hexane. The resultant solid was collected by filtration and dried under reduced pressure to give the title compound (1.55 g).

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated and to the obtained residue
  4. additionwere added chloroform and hexane
  5. filtrationThe resultant solid was collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-c7691dbc2da540c7b5aa94cd80fb18a4
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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