Triethylamine → HCID 57595403, compound

HRID 1786045Notes

Reaction equation

HRID 1786045 reaction equation
[NH2:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]([N:18]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[C:19](=[O:21])[CH3:20])[CH2:10][CH:9]2[CH3:29])=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:40][CH2:41][O:42][C:43](Cl)=[O:44].C([O-])([O-])=O.[Cs+].[Cs+]>C(Cl)Cl.CN(C=O)C>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([N:18]([C@H:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:8]([C:6](=[O:7])[C:5]3[CH:4]=[CH:3][C:2]([N:1]4[CH2:40][CH2:41][O:42][C:43]4=[O:44])=[CH:31][CH:30]=3)[C@@H:9]([CH3:29])[CH2:10]2)[C:19](=[O:21])[CH3:20])=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10796Cesium carbonateHCID 785282-Bromoethyl chloroformateHCID 68920856HCID 68920856, compound

Product 1

HCID 57595403HCID 57595403, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

N-[1-(4-Amino-benzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]-N-(4-chloro-phenyl)-acetamide (61 mg, 0.142 mmol) was dissolved in methylene chloride (2 mL) and was added triethylamine (0.100 mL, 0.700 mmol). 2-Bromoethylchloroformate (0.023 mL, 0.213 mmol) was added and the reaction was allowed to warm to room temperature. After 1 hour at room temperature, DMF (2 mL) and Cs2CO3 (100 mg, 0.307 mmol) were added and the mixture was stirred over night. The mixture was partitioned between methylene chloride and water; the methylene chloride layer was dried over MgSO4, filtered and concentrated. The crude residue was purified by silica gel chromatography (1/1 hexanes/ethyl acetate to 100% ethyl acetate gradient) to afford the product.

Workup

  1. customThe mixture was partitioned between methylene chloride and water
  2. dry with materialthe methylene chloride layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by silica gel chromatography (1/1 hexanes/ethyl acetate to 100% ethyl acetate gradient)
  6. customto afford the product

Sources & evidence

ORD record
ord-ae1f9b380e7349e2a92c334b994826ea
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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