Triethylamine → HCID 178429850, compound

HRID 2245370Notes

Reaction equation

HRID 2245370 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 (1H), 1.88 (1H), 2.10 (4H), 2.26 (3H), 3.15 (1H), 7.44 (1H), 7.63 (1H), 7.68 (1H), 7.90 (1H); 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-064dc825fc0c4e388367788e76fc54b7
Source dataset
uspto-grants-2010_03
Patent number
US07683084B2

Reaction notes

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