Triethylamine → HCID 136337086, compound

HRID 1802504Notes

Reaction equation

HRID 1802504 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:28])[C:9]=1[NH:10][C:11]1[C:20]2[CH:21]=[CH:22][N:23]=[C:24]([O:25][CH2:26][CH3:27])[C:19]=2[C:18]2[C:13](=[CH:14][CH:15]=[N:16][CH:17]=2)[N:12]=1)[C:5]#[N:6].C(N(CC)CC)C.[Cl-].[OH:37][NH3+:38]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5](=[N:38][OH:37])[NH2:6])[CH:7]=[C:8]([Cl:28])[C:9]=1[NH:10][C:11]1[C:20]2[CH:21]=[CH:22][N:23]=[C:24]([O:25][CH2:26][CH3:27])[C:19]=2[C:18]2[C:13](=[CH:14][CH:15]=[N:16][CH:17]=2)[N:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21645Hydroxylamine HClHCID 68424405HCID 68424405, compound

Product 1

HCID 136337086HCID 136337086, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3,5-dichloro-4-[(10-ethoxypyrido[4,3-c]-1,6-naphthyridin-6-yl)amino]benzonitrile (Example 160, Step 1) (200 mg, 0.49 mmol) in ethanol (6 mL) was added triethylamine (0.285 mL, 2.04 mmol) and hydroxyammonium chloride (105 mg, 1.51 mmol). The reaction mixture was heated to 80° C. for 3 h in a sealed tube. After cooling to room temperature, the solid was filtered, washed with ethanol and water and dried under vacuum to afford the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe solid was filtered
  3. washwashed with ethanol and water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-c8314ed020724a75bc497468f7bdacb9
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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