Hydrochloric Acid → HCID 57691168, compound

HRID 40399

Reaction equation

HRID 40399 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([CH2:13][C:14](OC(C)(C)C)=O)=[CH:8][CH:7]=2.[Cl:21][C:22]1[N:27]=[N:26][C:25]([NH:28][NH2:29])=[CH:24][CH:23]=1.Cl.[OH-].[Na+]>C(Cl)Cl.O>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]2[N:26]([C:14]([CH2:13][C:9]3[CH:10]=[C:11]4[C:6](=[CH:7][CH:8]=3)[N:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:12]4)=[N:29][N:28]=2)[N:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1007873-Chloro-6-hydrazinopyridazineHCID 59843087Tert-butyl 2-(3-methoxyquinolin-6-yl)acetate

Product 1

HCID 57691168HCID 57691168, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a 5 ml CEM microwave tube was added tert-butyl 2-(3-methoxyquinolin-6-yl)acetate (0.05 g, 0.2 mmol), 1-(6-chloropyridazin-3-yl)hydrazine (0.04 g, 0.3 mmol), water (0.5 mL) and hydrochloric acid (0.05 ml, 0.5 mmol). The vial was sealed and first heated at 90° C. for 30 min then placed into CEM microwave for 10 min. at 100° C., with 100 Watts of power via Powermax. The reaction mixture was adjusted the pH to 7 by adding 5 N NaOH—brown ppt. was generated. The brown ppt. was dissolved in DCM. The organic was washed with water, dried over MgSO4, and removed solvent in vacuo. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep®, P/N 68-2203-026, 12 g SiO2, DCM:EtOAc:MeOH=75%:20%:5%, Flow=30 mL/min). A peak at 25 min was collected. The solvent was removed in vacuo to afford the desired product as light yellowish solid. Wt: 20.0 mg. MS (ESI pos. ion) m/z: 326.53. Calc'd exact mass for C16H12ClN5O: 325.75.

Workup

  1. customThe vial was sealed
  2. washThe organic was washed with water
  3. dry with materialdried over MgSO4
  4. customremoved solvent in vacuo
  5. customThe crude product was purified
  6. customA peak at 25 min was collected
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d695cc1bcac14cd4b676cb42f2653bf4
Source dataset
uspto-grants-2013_09
Patent number
US08524900B2

Linked notes

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