Dichloromethane → HCID 10411615, compound

HRID 919003Notes

Reaction equation

HRID 919003 reaction equation
[C:1]([CH:5]([NH:12][NH:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][CH:16]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])([CH3:4])([CH3:3])[CH3:2].C[N:25]1CCO[CH2:27][CH2:26]1.[CH2:31](O)[C:32](N)([CH2:35][OH:36])[CH2:33][OH:34].[CH2:39](Cl)Cl>>[C:1]([CH:5]([N:12]([C:33](=[O:34])[C:32]1[CH:31]=[CH:27][CH:26]=[N:25][C:35]=1[O:36][CH3:39])[NH:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][CH:16]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 4

HCID 6344Dichloromethane3×HCID 6503Tris(hydroxymethyl)aminomethaneHCID 79724-MethylmorpholineHCID 59016620HCID 59016620, compound

Product 1

HCID 10411615HCID 10411615, compound

Procedure

In a 25 mL vial, 123.1 mg (0.388 mmol) of 4-ethyl-benzoic acid N′-(1-tert-butyl-heptyl)-hydrazide were dissolved in 5 mL CH2Cl2. 3 equivalents of PS-NMM (polystyrene SO2NH(CH2)3-morpholine, Argonaut Tech.) were added, followed by 3 mL CH2Cl2 to create a stirable suspension. One equivalent of acid chloride was added, and the reaction mixture was stirred overnight. The next day, 2 equivalents of AP-NCO rein (isocyante scavenger, ArgonautTech.) and 2 equivalents of AP-trisamine (polystyrene-CH2NHCH2CH2NH(CH2CH2NH2)2, Argonaut Tech.) were added with 3 mL CH2Cl2. The mixture was stirred for four hours and the resins were filtered. The reaction was analyzed by TLC, the solvent was removed, and the residue was dried under vacuum. After silica gel column chromatography using a 0-100% ether in hexane gradient, 107.5 mg of 2-methoxy-nicotinic acid N-(1-tert-butyl-heptyl)-N′-(4-ethyl-benzoyl)-hydrazide were isolated.

Workup

  1. stirringThe mixture was stirred for four hours
  2. filtrationthe resins were filtered
  3. customthe solvent was removed
  4. customthe residue was dried under vacuum

Sources & evidence

ORD record
ord-a56d7e4fd7434d0d9d98a8ce5d2a48f6
Source dataset
uspto-grants-2016_03
Patent number
US09272986B2

Reaction notes

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