Tetrahydrofuran → HCID 135430203, compound

HRID 2217910Notes

Reaction equation

HRID 2217910 reaction equation
[NH2:1][C:2](=[N:30]O)[CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([Cl:29])[C:15]=3[NH:19][C:20](=[O:28])[CH2:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[N:10]=2)[CH2:5][CH2:4]1.[C:32](N1C=CN=C1)(N1C=CN=C1)=[S:33].[O:44]1CCCC1>C(Cl)(Cl)Cl.CO>[Cl:29][C:14]1[C:15]([NH:19][C:20](=[O:28])[CH2:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([N:6]1[CH2:7][CH2:8][CH:3]([C:2]3[NH:1][C:32](=[O:44])[S:33][N:30]=3)[CH2:4][CH2:5]1)[CH:18]=[CH:17]2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 802641,1'-ThiocarbonyldiimidazoleHCID 86609749N-[2-[4-[Amino(hydroxyimino)methyl]-1-piperidinyl]-6-chloro-5-quinolinyl]-cyclohexaneacetamide

Product 1

HCID 135430203HCID 135430203, compound

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

To a stirred solution of N-[2-[4[amino(hydroxyimino)methyl]-1-piperidinyl]-6-chloro-5-quinolinyl]-cyclohexaneacetamide (Example 102(a)) (0.1 g) in tetrahydrofuran (2 mL) was added 1,1′-thiocarbonyldiimidazole (0.042 g). After stirring for 1 hour, silica (1 g) in chloroform:methanol (5:1) (12 mL) was added and the mixture was stirred for a further 12 hours. The solvent was removed under vacuum, the resulting solid was taken up in methanol (20 mL) and was purified by Varian NH2 cartridge (methanol (50 mL) and then acetic acid:methanol 10:90 as eluant) to afford the title product (0.041 g).

Workup

  1. stirringthe mixture was stirred for a further 12 hours
  2. customThe solvent was removed under vacuum
  3. customwas purified by Varian NH2 cartridge (methanol (50 mL)

Sources & evidence

ORD record
ord-b0f33582aa884f9f95f81aeb958b915e
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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