Dimethylcarbamoyl Chloride → (3S)-3-Amino-1-[(dimethylcarbamoyl)oxy]-6-phenoxy-3,4-dihydroquinolin-2(1H)-one

HRID 1926709Notes

Reaction equation

HRID 1926709 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].Cl.[NH2:8][C@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=2)[N:11]([OH:26])[C:10]1=[O:27]>N1C=CC=CC=1>[NH2:8][C@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=2)[N:11]([O:26][C:3](=[O:4])[N:2]([CH3:6])[CH3:1])[C:10]1=[O:27]

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 131729734HCID 131729734, compound

Product 1

HCID 59627155(3S)-3-Amino-1-[(dimethylcarbamoyl)oxy]-6-phenoxy-3,4-dihydroquinolin-2(1H)-oneYield 65%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Dimethylcarbamyl chloride (37 μL, 0.39 mmol) was added to a solution of (3S)-3-amino-1-hydroxy-6-phenoxy-3,4-dihydroquinolin-2(1H)-one, hydrochloride salt (93, Example 71) (100 mg, 0.33 mmol) in pyridine (2 mL). The reaction mixture was maintained at RT for 1.5 h, then concentrated in vacuo; the resulting residue was diluted with EtOAc (20 mL) and water (10 mL). The separated organic phase was washed with water (10 mL), dried over Mg2SO4, filtered, and concentrated in vacuo to provide the title compound as an oil (72 mg, 65%). LCMS m/z 253.0 [(M-dimethyl carbamic acid)+1]. 1H NMR (400 MHz, CD3OD) δ 2.94-3.02 (m, 1H), 3.02 (br s, 3H), 3.08 (dd, half of ABX pattern, J=15.5, 6.4 Hz, 1H), 3.17 (br s, 3H), 3.78 (dd, J=13.3, 6.3 Hz, 1H), 6.90-7.00 (m, 5H), 7.11 (ddt, J=7.7, 7.1, 1.1 Hz, 1H), 7.32-7.37 (m, 2H).

Workup

  1. concentrationconcentrated in vacuo
  2. additionthe resulting residue was diluted with EtOAc (20 mL) and water (10 mL)
  3. washThe separated organic phase was washed with water (10 mL)
  4. dry with materialdried over Mg2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-58a1f9fceabb466fb7e2d6639cd31627
Source dataset
uspto-grants-2012_05
Patent number
US08183238B2

Reaction notes

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