Triethylamine → HCID 68807323, compound

HRID 1796311Notes

Reaction equation

HRID 1796311 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@@H:9]1[C:21](O)=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:24][C:25]1[CH:35]=[CH:34][C:28]([C:29]([N:31]([CH3:33])[CH3:32])=[O:30])=[CH:27][C:26]=1[F:36].CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1.C(N(CC)CC)C>C(Cl)(Cl)Cl.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:16])[CH2:10][C@@H:9]1[C:21](=[O:22])[NH:24][C:25]1[CH:35]=[CH:34][C:28]([C:29](=[O:30])[N:31]([CH3:32])[CH3:33])=[CH:27][C:26]=1[F:36])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 221815204-Amino-3-fluoro-N,N-dimethylbenzamideHCID 68806846HCID 68806846, compound

Product 1

HCID 68807323HCID 68807323, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

Into a solution of 2 (1.25 g, 3.61 mmol) in CHCl3 (25 mL) was added 5 (0.66 g, 3.61 mmol), EEDQ (1.07 g, 4.32 mmol), and triethylamine (0.74 mL, 5.33 mmol). The solution was stirred at reflux for 19 h before cooling to RT and adding EtOAc. The solution was washed sequentially with 1N HCl, 0.1N NaOH, water, and brine, before drying over MgSO4 and concentrating under reduced pressure. The crude material was purified on a silica gel column eluted with 20% moving to 50% EtOAc in hexanes. Combined and concentrated pure fractions to give 6 (0.33 g, 18%). MS: APCI (AP+): 510.3 (M)+, (AP−): 508.4 (M)−.

Workup

  1. temperatureat reflux for 19 h
  2. washThe solution was washed sequentially with 1N HCl, 0.1N NaOH, water, and brine
  3. dry with materialbefore drying over MgSO4
  4. concentrationconcentrating under reduced pressure
  5. customThe crude material was purified on a silica gel column
  6. washeluted with 20%
  7. concentrationconcentrated pure fractions

Sources & evidence

ORD record
ord-ecae4f03b14e4efd947cc7c58ffb0f7c
Source dataset
uspto-grants-2006_04
Patent number
US07030141B2

Reaction notes

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