Dimethylcarbamoyl Chloride → HCID 71468974, compound

HRID 1501890Notes

Reaction equation

HRID 1501890 reaction equation
[F:1][C:2]1([F:30])[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:19](=[O:29])[N:20]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=4)[CH2:21][C:16]3=[C:15]3[C:10]=2[CH:11]=[CH:12][CH:13]=[N:14]3)[CH2:4][CH2:3]1.[H-].[Na+].[CH3:33][N:34]([CH3:38])[C:35](Cl)=[O:36]>CS(C)=O.C(OCC)(=O)C>[CH3:33][N:34]([CH3:38])[C:35](=[O:36])[O:28][C:24]1[CH:25]=[CH:26][CH:27]=[C:22]([N:20]2[CH2:21][C:16]3[C:17](=[CH:18][C:9]([CH2:8][N:5]4[CH2:6][CH2:7][C:2]([F:1])([F:30])[CH2:3][CH2:4]4)=[C:10]4[C:15]=3[N:14]=[CH:13][CH:12]=[CH:11]4)[C:19]2=[O:29])[CH:23]=1

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 71043057HCID 71043057, compound

Product 1

HCID 71468974HCID 71468974, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-[(4,4-difluoropiperidin-1-yl)methyl]-8-(3-hydroxyphenyl)-8,9-dihydro-7H-pyrrolo[3,4-h]quinolin-7-one (0.070 g, 0.17 mmol) in 3 mL of dimethylsulfoxide was added sodium hydride (0.034 g, 0.86 mmol). After 5 min, dimethyl carbamyl chloride (0.047 mL, 0.51 mmol) was added. The mixture was stirred at ambient temperature for 15 hr, diluted with ethyl acetate, washed 3× with brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via preparative reverse phase HPLC to provide the title compound that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 481.2066 for [M+H]+ [Calc'd for C26H27F2N4O3, [M+H]+=481.2046].

Workup

  1. washwashed 3× with brine
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via preparative reverse phase HPLC

Sources & evidence

ORD record
ord-ab3350d13f164d83a7c5588bd99638e3
Source dataset
uspto-grants-2015_12
Patent number
US09206200B2

Reaction notes

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