Triethylamine → HCID 68431412, compound

HRID 2092063Notes

Reaction equation

HRID 2092063 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][CH2:10][CH2:11][C:12](O)=[O:13])[N:5]=[CH:4][C:3]=1[NH:15][C@@H:16]1[CH2:21][C@@H:20]2[CH2:22][C@@H:18]([C:19]2([CH3:24])[CH3:23])[C@H:17]1[CH3:25].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[N:45]1[CH:50]=[CH:49][C:48]([CH2:51][NH2:52])=[CH:47][CH:46]=1>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][CH2:10][CH2:11][C:12]([NH:52][CH2:51][C:48]2[CH:49]=[CH:50][N:45]=[CH:46][CH:47]=2)=[O:13])[N:5]=[CH:4][C:3]=1[NH:15][C@@H:16]1[CH2:21][C@@H:20]2[CH2:22][C@@H:18]([C:19]2([CH3:23])[CH3:24])[C@H:17]1[CH3:25]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 773174-PyridinemethanamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68431968HCID 68431968, compound

Product 1

HCID 68431412HCID 68431412, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-{5-Bromo-6-oxo-4-[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylamino]pyridazin-1(6H)-yl}butanoic acid (38 mg, 0.091 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (35 mg, 0.182 mmol), 1-hydroxybenzotriazole anhydride (12 mg, 0.091 mmol) and triethylamine (25 μL, 0.182 mmol) in N,N-dimethylformamide (1 mL) were stirred with 4-picolylamine (25 μL, 0.182 mmol) at room temperature for 24 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=15/1) to give the desired product (30 mg, 58% 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=15/1)

Sources & evidence

ORD record
ord-27f9c9be23244f09843502497a09de5d
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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