Triethylamine → HCID 67246672, compound

HRID 2425754Notes

Reaction equation

HRID 2425754 reaction equation
Cl.[CH:2]([N:5]1[C:14]2[C:9](=[C:10]([CH3:15])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]([C:16]([NH:18][CH2:19][CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[O:17])[C:6]1=[O:26])([CH3:4])[CH3:3].Br[CH:28]([CH3:36])[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>O1CCCC1>[CH:2]([N:5]1[C:14]2[C:9](=[C:10]([CH3:15])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]([C:16]([NH:18][CH2:19][CH:20]2[CH2:25][CH2:24][N:23]([CH:28]([CH3:36])[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:22][CH2:21]2)=[O:17])[C:6]1=[O:26])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 545327tert-Butyl 2-bromopropanoateHCID 67245033HCID 67245033, compound

Product 1

HCID 67246672HCID 67246672, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-isopropyl-5-methyl-2-oxo-N-(piperidin-4-ylmethyl)-1,2-dihydroquinoline-3-carboxamide hydrochloride (467 mg, 0.98 mmol, step 4 in preparation 3), tert-butyl 2-bromopropanoate (0.24 mL, 1.47 mmol), and triethylamine (0.41 mL, 2.93 mmol) in tetrahydrofuran (30 mL) was stirred at 70° C. for 23 h. After cooling to room temperature, the mixture was poured onto saturated aqueous sodium hydrogen carbonate (100 mL), and the aqueous layer was extracted with dichloromethane (100 mL×2). The combined organic layer was dried over magnesium sulfate, and concentrated in vacuo. The residue was chromatographed on a column of silica gel eluting with ammonia/methanol/dichloromethane (0.1:1:30) to give 299 mg (65%) of the title compound as a yellow amorphous.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe aqueous layer was extracted with dichloromethane (100 mL×2)
  3. dry with materialThe combined organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on a column of silica gel eluting with ammonia/methanol/dichloromethane (0.1:1:30)

Sources & evidence

ORD record
ord-1a376291ffd84bd0a2b74d0c6dc488c9
Source dataset
uspto-grants-2011_06
Patent number
US07964727B2

Reaction notes

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