Triethylamine → HCID 57595400, compound

HRID 1786001Notes

Reaction equation

HRID 1786001 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.Cl[CH2:40][CH2:41][N:42]=[C:43]=[O:44]>C(Cl)Cl>[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][NH: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

5

Reactant 3

HCID 8471TriethylamineHCID 160352-Chloroethyl isocyanateHCID 68920856HCID 68920856, compound

Product 1

HCID 57595400HCID 57595400, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[1-(4-Amino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-(4-chloro-phenyl)-acetamide (156 mg, 0.373 mmol) was dissolved in methylene chloride (3 mL) and was added triethylamine (0.078 mL, 0.559 mmol) and 1-chloro-2-isocyanato-ethane 0.038 mL, 0.448 mmol). The reaction was stirred at room temperature over night, and the reaction was quenched with sat. aq. NaHCO3. The residue was partitioned between methylene chloride and water, then extracted three times with methylene chloride, dried over MgSO4, filtered and concentrated down. The crude residue was purified by silica gel chromatography (ethyl acetate) to afford the product.

Workup

  1. customthe reaction was quenched with sat. aq. NaHCO3
  2. customThe residue was partitioned between methylene chloride and water
  3. extractionextracted three times with methylene chloride
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated down
  7. customThe crude residue was purified by silica gel chromatography (ethyl acetate)
  8. customto afford the product

Sources & evidence

ORD record
ord-c5298b408298432e9b34470546c398e6
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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