Water → HCID 68432296, compound

HRID 2092106Notes

Reaction equation

HRID 2092106 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:9](=[O:10])[C:8]([Br:11])=[C:7]([NH:12][C@@H:13]2[CH2:18][C@@H:17]3[CH2:19][C@@H:15]([C:16]3([CH3:21])[CH3:20])[C@H:14]2[CH3:22])[CH:6]=[N:5]1.C(N(CC)CC)C.[N:30]1[CH:35]=[CH:34][C:33]([C:36](Cl)=[O:37])=[CH:32][CH:31]=1.O>ClCCl>[Br:11][C:8]1[C:9](=[O:10])[N:4]([CH2:3][CH2:2][NH:1][C:36]([C:33]2[CH:34]=[CH:35][N:30]=[CH:31][CH:32]=2)=[O:37])[N:5]=[CH:6][C:7]=1[NH:12][C@@H:13]1[CH2:18][C@@H:17]2[CH2:19][C@@H:15]([C:16]2([CH3:21])[CH3:20])[C@H:14]1[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 417436Pyridine-4-carbonyl chlorideHCID 68431688HCID 68431688, compound

Product 1

HCID 68432296HCID 68432296, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(2-Aminoethyl)-4-bromo-5-{[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]amino}pyridazin-3(2H)-one (28 mg, 0.0758 mmol) and triethylamine (21 μL, 0.152 mmol) in dichloromethane (1 mL) were stirred with pyridine-4-carbonyl chloride (20 mg, 0.112 mmol) at room temperature for 5 hours. After completion of the reaction, the reaction solution was mixed with water and extracted with ethyl acetate, and the extract was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/methanol=9/1) to give the desired product (19 mg, 52% yield).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialthe extract was dried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/methanol=9/1)

Sources & evidence

ORD record
ord-6045b6c0c2094cbfbe593ee05a88b386
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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