Triethylamine → HCID 24853066, compound

HRID 1260349Notes

Reaction equation

HRID 1260349 reaction equation
[CH3:1][C:2]1[S:6][C:5](=[NH:7])[N:4]([C:8]2[CH:21]=[CH:20][C:11]3[O:12][C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[O:15][C:10]=3[CH:9]=2)[CH:3]=1.C(N(CC)CC)C.[N:29]1([C:35](Cl)=[O:36])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>C(#N)C>[CH3:1][C:2]1[S:6]/[C:5](=[N:7]\[C:35]([N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[O:36])/[N:4]([C:8]2[CH:21]=[CH:20][C:11]3[O:12][C:13]([F:19])([F:18])[C:14]([F:16])([F:17])[O:15][C:10]=3[CH:9]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2420851-Piperidinecarbonyl chlorideHCID 15451838HCID 15451838, compound

Product 1

HCID 24853066HCID 24853066, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

The imine (Example 26A, 30 mg, 0.09 mmol) was dissolved in acetonitrile (1.5 mL). Triethylamine (19 μl, 0.18 mmol) was added followed by the 1-piperidinecarbonyl chloride (0.11 mmol). The reaction was heated at 65° C. overnight. The reaction mixture was cooled down and passed through a Si-amine cartridge (1 g, 1.6 mmol/g) to remove the excess carbamyl chloride eluting with additional acetonitrile. The resulting solution was dried and purified by reverse phase HPLC to supply the titled compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.40 (4 H), 1.53 (2 H), 2.20 (3 H), 3.43 (4 H), 7.24 (1 H), 7.63 (2 H), 7.83 (1 H); MS (ESI) m/z 432.2 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled down
  2. customto remove the excess carbamyl chloride eluting with additional acetonitrile
  3. customThe resulting solution was dried
  4. custompurified by reverse phase HPLC to supply the titled compound

Sources & evidence

ORD record
ord-80a7c0424d1e4525a8ec278ee9a95906
Source dataset
uspto-grants-2013_06
Patent number
US08470813B2

Reaction notes

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