Diisopropylethylamine → HCID 18331395, compound

HRID 2270546Notes

Reaction equation

HRID 2270546 reaction equation
C(OC([N:8]([CH2:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=O)(C)(C)C.Cl[C:25]1[N:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:26]=1[C:27]([OH:29])=[O:28].C(N(C(C)C)CC)(C)C>O1CCOCC1>[Cl:34][C:32]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[C:25]([NH:20][C:19]2[CH:21]=[CH:22][CH:23]=[C:17]([CH2:16][NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH:18]=2)[N:33]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 8540472,6-Dichloronicotinic acidHCID 18331424HCID 18331424, compound

Product 1

HCID 18331395HCID 18331395, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-(di-(t-butoxycarbonyl)aminomethyl)aniline (81 mg), 2,6-dichloronicotinic acid (90%, 53 mg), di-i-propylethylamine (64 mg) and 1,4-dioxane (1 ml) was heated under reflux for 3 days and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, methylene chloride:methanol=20:1) to give 24 mg of the titled compound (yield, 25%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 days
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (eluent, methylene chloride:methanol=20:1)

Sources & evidence

ORD record
ord-7e95024883e746aa853f08818b8750e2
Source dataset
uspto-grants-2001_12
Patent number
US06331553B1

Reaction notes

Loading…