Ammonium Chloride → HCID 66777349, compound

HRID 2091071Notes

Reaction equation

HRID 2091071 reaction equation
C1([CH:7]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]([OH:27])=O)=[N:23][CH:24]=2)[C:8]2[S:9][C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=3[C:12]=2[CH3:13])CCCCC1.[CH3:28][NH:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33].O.ON1[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl-].[NH4+]>CN(C)C=O.C(N(CC)CC)C>[CH:42]1([CH:7]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]([N:29]([CH3:28])[CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:27])=[N:23][CH:24]=2)[C:8]2[S:9][C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=3[C:12]=2[CH3:13])[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66777565HCID 66777565, compound

Product 1

HCID 66777349HCID 66777349, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 5-{[cyclohexyl(3-methyl-1-benzothiophen-2-yl)methyl]amino}pyridine-2-carboxylic acid (200 mg) synthesized above, ethyl 3-(methylamino)propanoate (104 mg), 1-hydroxybenzotriazole monohydrate (121 mg), triethylamine (220 μL) and N,N-dimethylformamide (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (151 mg), and the mixture was stirred at room temperature for 4 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30-70% ethyl acetate/hexane) to give the title object compound (141 mg, 54%) as a white solid.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (30-70% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9d6cf3025b964c00a8ce01e5491b7e16
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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