Ammonium Chloride → Ethyl 3-{[(4-{[cyclohexyl(3-methylthieno[2,3-c]pyridin-2-yl)methyl]amino}phenyl)carbonyl](methyl)amino}propanoate

HRID 2091290Notes

Reaction equation

HRID 2091290 reaction equation
[CH:1]1([CH:7]([NH:18][C:19]2[CH:27]=[CH:26][C:22](C(O)=O)=[CH:21][CH:20]=2)[C:8]2[S:16][C:11]3=[CH:12]N=[CH:14][CH:15]=[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].[OH2:37].ON1C2C=CC=C[C:42]=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl-].[NH4+:61]>CN(C)C=O.C(N(CC)CC)C>[CH:1]1([CH:7]([NH:18][C:19]2[CH:27]=[CH:26][C:22]([C:28]([N:29]([CH3:42])[CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:37])=[CH:21][CH:20]=2)[C:8]2[S:16][C:11]3=[CH:12][N:61]=[CH:14][CH:15]=[C:10]3[C:9]=2[CH3:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 867618284-{[Cyclohexyl(3-methylthieno[2,3-c]pyridin-2-yl)methyl]amino}benzoic acid

Product 1

HCID 66777782Ethyl 3-{[(4-{[cyclohexyl(3-methylthieno[2,3-c]pyridin-2-yl)methyl]amino}phenyl)carbonyl](methyl)amino}propanoateYield 58%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 4-{[cyclohexyl(3-methylthieno[2,3-c]pyridin-2-yl)methyl]amino}benzoic acid (202 mg) synthesized above, ethyl 3-(methylamino)propanoate (104 mg), 1-hydroxybenzotriazole monohydrate (122 mg), triethylamine (222 μL) and N,N-dimethylformamide (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (152 mg), and the mixture was stirred at room temperature for 1 day. 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 (30-100% ethyl acetate/hexane, then 0-10% methanol/acetic acid) to give the title object compound (151 mg, 58%) as a pale-yellow 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 (30-100% ethyl acetate/hexane

Sources & evidence

ORD record
ord-215dfadcf27a4cf1abc837127eb096cc
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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