Ethylamine → HCID 68835435, compound

HRID 2112977Notes

Reaction equation

HRID 2112977 reaction equation
[CH3:1][C:2]1[C:3]([C:8]2[N:13]3[N:14]=[C:15]([NH2:17])[N:16]=[C:12]3[CH:11]=[C:10]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.S([N:34]=[C:35]=[O:36])(C1C=CC(C)=CC=1)(=O)=O.N[CH2:38]C>CN(C=O)C.C1COCC1>[CH3:38][NH:34][C:35]([NH:17][C:15]1[N:16]=[C:12]2[CH:11]=[C:10]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH:9]=[C:8]([C:3]3[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=3)[N:13]2[N:14]=1)=[O:36]

Participants

6

Reactant 3

HCID 6341EthylamineHCID 77703p-Toluenesulfonyl isocyanateHCID 68834797HCID 68834797, compound

Product 1

HCID 68835435HCID 68835435, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product of Step 1 (240 mg, 0.79 mmol) was taken up in DMF (2 mL) to which was added TosNCO (0.31 g, 1.6 mmol) all at once. The mixture was stirred at room temperature for 1 h whereon a 2 M solution of H2NEt (3 mL, 6 mmol) in THF was added. The homogeneous solution was microwaved at 100° C. for 10 min. On cooling, SiO2 was added and the solvent was removed. Column chromatography afforded the title compound. MS m/z 374 (M+H+).

Workup

  1. additionwas added
  2. customThe homogeneous solution was microwaved at 100° C. for 10 min
  3. temperatureOn cooling
  4. additionSiO2 was added
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-e479915f0a564acabce1c56148d511a6
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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