Triethylamine → HCID 74015319, compound

HRID 1160752Notes

Reaction equation

HRID 1160752 reaction equation
[CH2:1]([N:5]([CH2:8][CH:9]([CH3:11])[CH3:10])[CH:6]=O)[CH:2]([CH3:4])[CH3:3].P(Cl)(Cl)(Cl)=O.[Cl:17][C:18]1[N:19]=[C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[N:22][N:21]2[C:27]=1[S:28]([NH2:31])(=[O:30])=[O:29].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:17][C:18]1[N:19]=[C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[N:22][N:21]2[C:27]=1[S:28]([N:31]=[CH:6][N:5]([CH2:8][CH:9]([CH3:11])[CH3:10])[CH2:1][CH:2]([CH3:4])[CH3:3])(=[O:30])=[O:29]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 75770N,N-Bis(2-methylpropyl)formamideHCID 516892Sodium BicarbonateHCID 14422383HCID 14422383, compound

Product 1

HCID 74015319HCID 74015319, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N,N-Diisobutylformamide (5.44 g, 34.5 mmol) was dissolved in chloroform (25.0 mL) and cooled in an ice-sodium chloride bath, and phosphorus oxychloride (3.22 mL, 34.5 mmol) was added dropwise thereto at −2° C. or less. After the mixture was stirred at −2° C. or less for 30 minutes, 2,6-dichloroimidazo[1,2-b]pyridazin-3-ylsulfonamide (6.15 g, 23.0 mmol) was added thereto. After the mixture was stirred at −10° C. for 10 minutes, triethylamine (19.3 mL, 138 mmol) was added dropwise over 20 minutes to the solution at 5° C. or less. The mixture was stirred for 1 hour at 0° C. or less and for 1 hour at room temperature, then poured into an aqueous saturated sodium bicarbonate and extracted 5 times with chloroform. The extracts were combined, dehydrated over anhydrous magnesium sulfate and concentrated under reduced pressure. The residues were purified by silica gel column chromatography (ethyl acetate:hexane=1:1) to give the title compound as pale yellow crystals. The yield was 5.58 g (59.6%).

Workup

  1. temperaturecooled in an ice-sodium chloride bath
  2. customat −2° C. or less
  3. stirringAfter the mixture was stirred at −10° C. for 10 minutes
  4. stirringThe mixture was stirred for 1 hour at 0° C. or less and for 1 hour at room temperature
  5. extractionextracted 5 times with chloroform
  6. concentrationconcentrated under reduced pressure
  7. customThe residues were purified by silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-8d8ea320716a442ab3077293a289e8fb
Source dataset
uspto-grants-2010_10
Patent number
US07816526B2

Reaction notes

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