Ammonium Chloride → HCID 66872348, compound

HRID 1967487Notes

Reaction equation

HRID 1967487 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH:9][C:10]([C:12]2[CH:13]=[C:14]([S:18]([N:21]3[CH2:26][CH2:25][CH2:24][CH:23]([C:27](O)=[O:28])[CH2:22]3)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=2)=[O:11])=[N:5][CH:6]=[CH:7][CH:8]=1.C([N:33](CC)C(C)C)(C)C.[Cl-].[NH4+].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.O>[CH3:1][O:2][C:3]1[C:4]([NH:9][C:10]([C:12]2[CH:13]=[C:14]([S:18]([N:21]3[CH2:26][CH2:25][CH2:24][CH:23]([C:27]([NH2:33])=[O:28])[CH2:22]3)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=2)=[O:11])=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66872362HCID 66872362, compound

Product 1

HCID 66872348HCID 66872348, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The compound (50 mg) obtained in Example 56 was dissolved in DMF (1.0 mL), then N,N-diisopropylethylamine (0.030 mL), ammonium chloride (8 mg), 1-hydroxybenzotriazole hydrate (22 mg) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (27 mg) were added thereto in that order, and stirred at room temperature for 3 days. Water was added to the reaction liquid, and extracted four times with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried with sodium sulfate. The drying agent was removed through filtration, and the solvent was evaporated off under reduced pressure. The residue was purified through silica gel column chromatography (methanol/chloroform=from 0% to 20%, gradient) to give the entitled compound (37 mg, 74%) as a colorless solid.

Workup

  1. extractionextracted four times with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried with sodium sulfate
  4. customThe drying agent was removed through filtration
  5. customthe solvent was evaporated off under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (methanol/chloroform=from 0% to 20%, gradient)

Sources & evidence

ORD record
ord-10d5bc9a688044098f97046ca7d2d0a8
Source dataset
uspto-grants-2013_04
Patent number
US08420823B2

Reaction notes

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