Triethylamine → HCID 59320311, compound

HRID 655285Notes

Reaction equation

HRID 655285 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:17][N:18]1[CH:22]=[C:21]([C:23]2[CH:24]=[N:25][C:26]3[C:31]([CH:32]=2)=[CH:30][C:29]([CH2:33][C:34](Cl)=O)=[CH:28][CH:27]=3)[CH:20]=[N:19]1>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:34]([CH2:33][C:29]3[CH:30]=[C:31]4[C:26](=[CH:27][CH:28]=3)[N:25]=[CH:24][C:23]([C:21]3[CH:20]=[N:19][N:18]([CH3:17])[CH:22]=3)=[CH:32]4)=[N:9][N:8]=2)[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1007873-Chloro-6-hydrazinopyridazineHCID 86641544HCID 86641544, compound

Product 1

HCID 59320311HCID 59320311, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

(6-Chloro-pyridazin-3-yl)-hydrazine (190 mg, 1.315 mmol) was dissolved in dimethylformamide followed by the addition of triethylamine (3 eq). This mixture was stirred for 5 minutes. The mixture became dark green and then was cooled 0° C. A solution of [3-(1-methyl-1H-pyrazol-4-yl)-quinolin-6-yl]acetyl chloride (375 mg, 1.315 mmol) in dimethylformamide was added dropwise and the reaction mixture turned dark yellow, and stirred for one hour. After such time mixture was concentrated to dryness then taken up in acetic acid (10 mL) and stirred at 60° C. for 16 hours. The solvent was removed in vacuo and the residue partitioned between ethyl acetate and water, and the aqueous phase further extracted with ethyl acetate. The combined organics purified via flash column chromatography (SiO2, CH2Cl2, methanol gradient 0 to 10%) to return the title compound (217 mg, 42% yield). Analytical data presented in Table 2.

Workup

  1. stirringstirred for one hour
  2. concentrationAfter such time mixture was concentrated to dryness
  3. stirringstirred at 60° C. for 16 hours
  4. customThe solvent was removed in vacuo
  5. customthe residue partitioned between ethyl acetate and water
  6. extractionthe aqueous phase further extracted with ethyl acetate
  7. customThe combined organics purified via flash column chromatography (SiO2, CH2Cl2, methanol gradient 0 to 10%)

Sources & evidence

ORD record
ord-7ece3960f7d140bfb95549340cc1a70f
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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