N,N-Dimethylpiperidin-4-amine → HCID 49783679, compound

HRID 1184371Notes

Reaction equation

HRID 1184371 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([S:13][C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=2[CH3:21])=[C:7]([S:9](Cl)(=[O:11])=[O:10])[CH:8]=1)#[N:2].[CH3:22][N:23]([CH3:30])[CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>C(Cl)Cl>[CH3:22][N:23]([CH3:30])[CH:24]1[CH2:29][CH2:28][N:27]([S:9]([C:7]2[CH:8]=[C:3]([CH:4]=[CH:5][C:6]=2[S:13][C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=2[CH3:21])[C:1]#[N:2])(=[O:11])=[O:10])[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 417391N,N-Dimethylpiperidin-4-amineHCID 59548940HCID 59548940, compound

Product 1

HCID 49783679HCID 49783679, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 26 (0.200 g, 0.59 mmol) in DCM was added TEA (0.090 g, 0.89 mmol) and 4-dimethylaminopiperidine (0.114 g, 0.89 mmol). The reaction was monitored by HPLC. The reaction was complete after stirring at room temperature for 16 hrs. DCM was removed in vacuo, and the resulting solid was dissolved in a minimal amount of DCM and purified with chromatography with a gradient of 10 to 30% MeOH in DCM. Pure fractions were combined and evaporated in vacuo to yield an oil, which was triturated with DCM and hexanes, and then filtered to yield compound 72 as a peach solid (0.124 g, 49% yield). HPLC purity: 96.5%; 1H NMR (500 MHz, DMSO-d6): δ 8.22 (d, J=2 Hz, 1H), 7.84 (dd, J1=2 Hz, J2=8 Hz, 1H), 7.41 (d, J=6 Hz, 1H), 7.39 (s, 1H), 7.34 (d, J=8 Hz, 1H), 6.70 (d, J=8 Hz, 1H), 3.8 (d, J=13 Hz, 2H), 2.84 (t, J=12 Hz, 2H), 2.31 (s, 3H), 2.26 (m, 1H), 2.25 (s, 3H), 2.15 (s, 6H), 1.79 (d, J=12 Hz, 2H), 1.43 (m, 2H); MS (ESI, EI+): m/z=430 (MH+); melting point: 136-139° C.

Workup

  1. customDCM was removed in vacuo
  2. dissolutionthe resulting solid was dissolved in a minimal amount of DCM
  3. custompurified with chromatography with a gradient of 10 to 30% MeOH in DCM
  4. customevaporated in vacuo
  5. customto yield an oil, which
  6. customwas triturated with DCM and hexanes
  7. filtrationfiltered

Sources & evidence

ORD record
ord-6234c7c1fa634fec8f2594750bdde623
Source dataset
uspto-grants-2014_03
Patent number
US08669247B2

Reaction notes

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