Triethylamine → HCID 178429850, compound

HRID 1260350Notes

Reaction equation

HRID 1260350 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.[CH:29]1([C:33](Cl)=[O:34])[CH2:32][CH2:31][CH2:30]1>C(#N)C>[CH3:1][C:2]1[S:6]/[C:5](=[N:7]\[C:33]([CH:29]2[CH2:32][CH2:31][CH2:30]2)=[O:34])/[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 78705Cyclobutanecarbonyl chlorideHCID 15451838HCID 15451838, compound

Product 1

HCID 178429850HCID 178429850, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

The imine (Example 26A, 30 mg, 0.09 mmol) was dissolved in 1.5 ml acetonitrile (1.5 mL). Triethylamine (19 μl, 0.18 mmol) was added followed by the cyclobutanecarbonyl 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 carbonyl chloride eluting with additional acetonitrile. The resulting solution was dried and purified by reverse phase HPLC. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.75 (1 H), 1.88 (1 H), 2.10 (4 H), 2.26 (3 H), 3.15 (1 H), 7.44 (1 H), 7.63 (1 H), 7.68 (1 H), 7.90 (1 H); MS (ESI) m/z 403.0 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-0c22515e07a24f30b6b9df3ea69524a0
Source dataset
uspto-grants-2013_06
Patent number
US08470813B2

Reaction notes

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