Dimethylformamide → HCID 68429314, compound

HRID 2092117Notes

Reaction equation

HRID 2092117 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH:9]2[CH2:12][CH2:11][CH:10]2CC(O)=O)[N:5]=[CH:4][C:3]=1[NH:17][C@@H:18]1[CH2:23][C@@H:22]2[CH2:24][C@@H:20]([C:21]2([CH3:26])[CH3:25])[C@H:19]1[CH3:27].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[N:47]1[CH:52]=[CH:51][C:50]([CH2:53][NH2:54])=[CH:49][CH:48]=1.CN(C)[CH:57]=[O:58]>C(OCC)(=O)C>[Br:1][C:2]1[C:7](=[O:8])[N:6]([C:9]2([C:57]([NH:54][CH2:53][C:50]3[CH:51]=[CH:52][N:47]=[CH:48][CH:49]=3)=[O:58])[CH2:12][CH2:11][CH2:10]2)[N:5]=[CH:4][C:3]=1[NH:17][C@@H:18]1[CH2:23][C@@H:22]2[CH2:24][C@@H:20]([C:21]2([CH3:25])[CH3:26])[C@H:19]1[CH3:27]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 773174-PyridinemethanamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68429254HCID 68429254, compound

Product 1

HCID 68429314HCID 68429314, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-(5-Bromo-6-oxo-4-{[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]amino}pyridazin-1(6H)-yl)cyclobutaneacetic acid (108.7 mg, 0.256 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (98.2 mg, 0.512 mmol), 1-hydroxybenzotriazole anhydride (10.8 mg, 0.08 mmol) and triethylamine (71.4 μL, 0.512 mmol) in N,N-dimethylformamide (1 mL) were stirred with 4-picolylamine (51.3 μL, 0.512 mmol) at room temperature for 22 hours. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/methanol=20/1) to give the desired product (53.8 mg, 41% yield).

Workup

  1. additionwas added
  2. washthe organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/methanol=20/1)

Sources & evidence

ORD record
ord-9ffd5b45f54a436f90f7998adf6e8125
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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