Ethyl isothiocyanate → HCID 178465507, compound

HRID 1471817Notes

Reaction equation

HRID 1471817 reaction equation
[C:1]1([N:7]2[C:15](=[O:16])[C:14]3[C:9]([C:10]4[CH:19]=[CH:18][NH:17][C:11]=4[NH:12][CH:13]=3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.[CH2:29]([N:31]=[C:32]=[S:33])[CH3:30]>CN(C)C=O>[CH2:29]([NH:31][C:32]([N:17]1[C:11]2[NH:12][CH:13]=[C:14]3[C:15](=[O:16])[N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:8]=[C:9]3[C:10]=2[CH:19]=[CH:18]1)=[S:33])[CH3:30]

Participants

5

Reactant 3

HCID 10966Ethyl isothiocyanateHCID 81531DiisopropylethylamineHCID 178515238HCID 178515238, compound

Product 1

HCID 178465507HCID 178465507, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of pyrrolo-pyridine 16 in dimethylformamide under an atmosphere of nitrogen and 3 equivalents of di-iso-propylethylamine (3 eq.) was added 3 equivalents of ethylisothiocyanate. The reaction mixture was stirred in a microwave at 100° C. for 3 hours. The crude reaction mixture was concentrated in vacuo and purified by column chromatography to afford compound 17e. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.22-1.42 (m, 3H) 3.68-3.93 (m, 2H) 6.72-6.90 (m, 1H) 7.19-7.38 (m, 1H) 7.42-7.64 (m, 2H) 7.77-7.96 (m, 2H) 8.27-8.59 (m, 1H) 8.61-8.81 (m, 1H) 12.10-12.38 (m, 1H) 12.37-12.57 (m, 1H).

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated in vacuo
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-2bf8065ae052437c846af473844cf1e7
Source dataset
uspto-grants-2015_04
Patent number
US09012470B2

Reaction notes

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