Azobisisobutyronitrile → HCID 24768284, compound

HRID 2416189Notes

Reaction equation

HRID 2416189 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH2:7][CH:8]([C:16]3[N:17]=[C:18]([C:21]4[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=4)[S:19][CH:20]=3)[C:9](=[O:15])[NH:10][C:11]=2[CH:12]=[CH:13][CH:14]=1)=[O:4].C1C(=O)N(Br)C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH:7]=[C:8]([C:16]3[N:17]=[C:18]([C:21]4[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=4)[S:19][CH:20]=3)[C:9](=[O:15])[NH:10][C:11]=2[CH:12]=[CH:13][CH:14]=1)=[O:4]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 69451615HCID 69451615, compound

Product 1

HCID 24768284HCID 24768284, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
85 °C

Procedure

In an oven-dried, 100-mL, round-bottomed flask was placed 1,2,3,4-tetrahydro-2-oxo-3-[2-(4-pyridyl)-4-thiazolyl]-5-quinolinecarboxylic acid methyl ester (Step a, 60 mg, 0.16 mmol), NBS (Aldrich, 32 mg, 0.18 mmol), and AIBN (Aldrich, 5 mg, 0.03 mmol) in CCl4 (10 mL). The mixture was heated to 85° C. for 2 h, cooled to RT, and quenched with 2N NH3 in MeOH (5 mL). The crude product was concentrated in vacuo, and the resulting solid was filtered, washed with H2O (3×5 mL), and MeOH (1×2 mL) to afford 1,2-dihydro-2-oxo-3-[2-(4-pyridyl)-4-thiazolyl]-5-quinoline carboxylic acid methyl ester as a yellow solid: Mp: >250° C. MS m/z: 364 (M+1).

Workup

  1. temperaturecooled to RT
  2. customquenched with 2N NH3 in MeOH (5 mL)
  3. concentrationThe crude product was concentrated in vacuo
  4. filtrationthe resulting solid was filtered
  5. washwashed with H2O (3×5 mL), and MeOH (1×2 mL)

Sources & evidence

ORD record
ord-2ca6a184dc74437182bcdcc705e20fa6
Source dataset
uspto-grants-2004_11
Patent number
US06822097B1

Reaction notes

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