Acetyl chloride → HCID 59320345, compound

HRID 655298Notes

Reaction equation

HRID 655298 reaction equation
[NH:1]1[CH2:4][CH:3]([N:5]2[CH:9]=[C:8]([C:10]3[CH:11]=[N:12][C:13]4[C:18]([CH:19]=3)=[CH:17][C:16]([CH2:20][C:21]3[N:25]5[N:26]=[C:27]([CH3:30])[CH:28]=[CH:29][C:24]5=[N:23][N:22]=3)=[CH:15][CH:14]=4)[CH:7]=[N:6]2)[CH2:2]1.C(N(CC)CC)C.[C:38](Cl)(=[O:40])[CH3:39]>ClCCl.O>[CH3:30][C:27]1[CH:28]=[CH:29][C:24]2[N:25]([C:21]([CH2:20][C:16]3[CH:17]=[C:18]4[C:13](=[CH:14][CH:15]=3)[N:12]=[CH:11][C:10]([C:8]3[CH:7]=[N:6][N:5]([CH:3]5[CH2:4][N:1]([C:38](=[O:40])[CH3:39])[CH2:2]5)[CH:9]=3)=[CH:19]4)=[N:22][N:23]=2)[N:26]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 59320197HCID 59320197, compound

Product 1

HCID 59320345HCID 59320345, compoundYield 15.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To 3-(1-azetidin-3-yl-1H-pyrazol-4-yl)-6-(6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-quinoline (25 mg, 0.063 mmol) in dichloromethane (1 mL) was added triethylamine (9.7 uL, 0.069 mmol) followed by acetyl chloride (5.0 uL, 0.069 mmol). The mixture was stirred at room temperature overnight. The reaction was diluted with water and the product extracted into dichloromethane. The reaction was diluted with water and extracted into dichloromethane and washed with water. The filtrate was concentrated in vacuo onto silica gel and purified by flash chromatography (SiO2, CH2Cl2:CH3OH 100:0-90:10) to return the title compound (4.20 mg, 15% yield). Analytical data presented in Table 2.

Workup

  1. extractionthe product extracted into dichloromethane
  2. additionThe reaction was diluted with water
  3. extractionextracted into dichloromethane
  4. washwashed with water
  5. concentrationThe filtrate was concentrated in vacuo onto silica gel
  6. custompurified by flash chromatography (SiO2, CH2Cl2:CH3OH 100:0-90:10)

Sources & evidence

ORD record
ord-f1a573b8cc42454a8c7a5604178eaa28
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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