Pyridine → HCID 135448269, compound

HRID 2217909Notes

Reaction equation

HRID 2217909 reaction equation
[NH2:1][C:2](=[N:30][OH:31])[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.N1C=CC=CC=1.C(C(CCCC)[CH2:41][O:42]C(Cl)=O)C>ClCCl>[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:41](=[O:42])[O:31][N:30]=3)[CH2:4][CH2:5]1)[CH:18]=[CH:17]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 627832-Ethylhexyl chloroformateHCID 86609749N-[2-[4-[Amino(hydroxyimino)methyl]-1-piperidinyl]-6-chloro-5-quinolinyl]-cyclohexaneacetamide

Product 1

HCID 135448269HCID 135448269, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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) and pyridine (0.02 mL) in dichloromethane (5 mL) at 0° C. was added 2-ethylhexylchloroformate (0.064 mL). After 10 minutes the reaction was allowed to warm to room temperature and was then stirred for 2 hours. The solvent was removed under vacuum and the resulting solid was transferred to a 10 mL microwave vial with isohexane (3 mL) and heated within a microwave at 140° C. for 20 minutes. The reaction mixture was filtered and the solid was taken up in boiling methanol (20 mL) and purified by Varian NH2 cartridge (methanol (50 mL) and then acetic acid:methanol 10:90 as eluant) to afford the title product (0.042 g).

Workup

  1. customThe solvent was removed under vacuum
  2. temperatureheated within a microwave at 140° C. for 20 minutes
  3. filtrationThe reaction mixture was filtered
  4. custompurified by Varian NH2 cartridge (methanol (50 mL)

Sources & evidence

ORD record
ord-a90cc9751bde4dec90c59d066ec12a4b
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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