Ammonium Chloride → HCID 68628434, compound

HRID 2091300Notes

Reaction equation

HRID 2091300 reaction equation
[CH:1]1([CH:7]([NH:18][C:19]2[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=2)[C:8]2[S:16][C:15]3[CH:14]=[CH:13][N:12]=[CH:11][C:10]=3[C:9]=2[CH3:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:28][NH:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl-].[NH4+]>CN(C)C=O.C(N(CC)CC)C>[CH:1]1([CH:7]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([C:23]([N:29]([CH3:28])[CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:24])=[CH:26][CH:27]=2)[C:8]2[S:16][C:15]3[CH:14]=[CH:13][N:12]=[CH:11][C:10]=3[C:9]=2[CH3:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 86761829HCID 86761829, compound

Product 1

HCID 68628434HCID 68628434, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 4-{[cyclohexyl(3-methylthieno[3,2-c]pyridin-2-yl)methyl]amino}benzoic acid (209 mg) synthesized in Example A138(4), ethyl 3-(methylamino)propanoate (108 mg), 1-hydroxybenzotriazole monohydrate (126 mg), triethylamine (229 μL) and N,N-dimethylformamide (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (158 mg), and the mixture was stirred overnight at room temperature. 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 (60-100% ethyl acetate/hexane, then 0-10% methanol/ethyl acetate) to give the title object compound (180 mg, 66%) as a colorless oil.

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 (60-100% ethyl acetate/hexane

Sources & evidence

ORD record
ord-3681fab1904f402f9df8a065e135833a
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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