Pyridine → HCID 15231548, compound

HRID 1081482Notes

Reaction equation

HRID 1081482 reaction equation
[CH2:1]([O:3][C:4]1[CH:31]=[CH:30][C:7]2[N:8]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][C:22]=3[O:28][CH3:29])(=[O:20])=[O:19])[C:9](=[O:17])[N:10]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[C:6]=2[CH:5]=1)[CH3:2].N1C=CC=CC=1.[CH3:38][C:39]1[CH:47]=[CH:46][CH:45]=[CH:44][C:40]=1[C:41](Cl)=[O:42]>C(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:31]=[CH:30][C:7]2[N:8]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:41]([C:40]4[CH:44]=[CH:45][CH:46]=[CH:47][C:39]=4[CH3:38])=[O:42])=[CH:23][C:22]=3[O:28][CH3:29])(=[O:19])=[O:20])[C:9](=[O:17])[N:10]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[C:6]=2[CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 702762-Methylbenzoyl chlorideHCID 15231545HCID 15231545, compound

Product 1

HCID 15231548HCID 15231548, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.46 g of the compound prepared in Example 5 step B), 20 ml of DCM and 0.5 g of pyridine were mixed at 20° C. and 0.18 g of 2-methylbenzoyl chloride in 10 ml of DCM was then added. The reaction mixture was stirred for 16 hours and then concentrated under vacuum. The residue was washed with water, with 1N hydrochloric acid, with 10% sodium carbonate and then with water. It was dried over sodium sulfate and the solvent was then evaporated off to dryness to give the expected product in the form of a white solid, which crystallized from isopropyl ether. m=0.3 g. M.p.=180° C.

Workup

  1. concentrationconcentrated under vacuum
  2. washThe residue was washed with water, with 1N hydrochloric acid, with 10% sodium carbonate
  3. dry with materialIt was dried over sodium sulfate
  4. customthe solvent was then evaporated off to dryness

Sources & evidence

ORD record
ord-62977c39fe194ba2a9e432c64775525b
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

Loading…