Triethylamine → HCID 68429130, compound

HRID 2092066Notes

Reaction equation

HRID 2092066 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH:9]([CH3:13])[C:10](O)=[O:11])[N:5]=[CH:4][C:3]=1[NH:14][C@@H:15]1[CH2:20][C@@H:19]2[CH2:21][C@@H:17]([C:18]2([CH3:23])[CH3:22])[C@H:16]1[CH3:24].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[N:44]1[CH:49]=[CH:48][C:47]([CH2:50][NH2:51])=[CH:46][CH:45]=1>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH:9]([CH3:13])[C:10]([NH:51][CH2:50][C:47]2[CH:48]=[CH:49][N:44]=[CH:45][CH:46]=2)=[O:11])[N:5]=[CH:4][C:3]=1[NH:14][C@@H:15]1[CH2:20][C@@H:19]2[CH2:21][C@@H:17]([C:18]2([CH3:22])[CH3:23])[C@H:16]1[CH3:24]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 773174-PyridinemethanamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68431453HCID 68431453, compound

Product 1

HCID 68429130HCID 68429130, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-{5-Bromo-6-oxo-4-[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylamino]pyridazin-1(6H)-yl}propanoic acid (40 mg, 0.099 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (38 mg, 0.199 mmol), 1-hydroxybenzotriazole anhydride (4 mg, 0.03 mmol) and triethylamine (28 μL, 0.199 mmol) in N,N-dimethylformamide (1 mL) were stirred with 4-picolylamine (20 μL, 0.199 mmol) at room temperature for 17.5 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 magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (chloroform/methanol=20/1) to give the desired product (25 mg, 52% 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 magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-ee037bc6ff7941de91caac8af82fe7e2
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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