Pyridine → HCID 68633817, compound

HRID 1928856Notes

Reaction equation

HRID 1928856 reaction equation
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:21])[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.N1C=CC=CC=1.Cl[C:29]([O:31][C:32]1C=CC([N+]([O-])=O)=CC=1)=[O:30]>ClCCl>[CH3:32][O:31][C:29](=[O:30])[NH:21][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([NH:10][C@H:1]1[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][CH2:2]1)[CH:20]=[CH:19]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 57860958(R)-N2-Indan-1-yl-quinoline-2,6-diamine

Product 1

HCID 68633817HCID 68633817, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of (R)—N2-indan-1-yl-quinoline-2,6-diamine (1.2 g, 4.36 mmol) and pyridine (0.35 mL, 4.36 mmol) in dichloromethane (25 mL) at 0° C. was added 4-nitrophenyl chloroformate (878 mg, 4.6 mmol) and the mixture was stirred at 23° C. for 2 h resulting in a yellow suspension. Added tetrahydrofuran, filtered the solid off, dissolved in dichloromethane and methanol, coated on silica gel. Removal of the solvent in vacuum left a brown foam, which after silica gel column chromatography was crystallized from dichloromethane/diethyl ether to give the title compound as a yellow foam (500 mg, 34%); MS: m/e=334.2 (M+H+).

Workup

  1. customresulting in a yellow suspension
  2. filtrationAdded tetrahydrofuran, filtered the solid off,
  3. dissolutiondissolved in dichloromethane
  4. customRemoval of the solvent in vacuum
  5. waitleft a brown foam, which after silica gel column chromatography
  6. customwas crystallized from dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-0380bcf685f8427aafb027ca0471240f
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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