1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 66726198, compound

HRID 1042163Notes

Reaction equation

HRID 1042163 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]1[N:12]=[CH:11][C:10]([O:13][C:14]2[CH:15]=[C:16]3[C:20](=[C:21]([O:23][CH:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[CH:22]=2)[NH:19][C:18]([C:30]2[S:31][CH:32]([CH2:35][C:36](O)=[O:37])[CH2:33][N:34]=2)=[CH:17]3)=[CH:9][CH:8]=1.O.O[N:41]1[C:45]2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.Cl.CN>CN(C)C=O.CCCCCC.C(OCC)(=O)C.O.C(N(CC)CC)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]1[N:12]=[CH:11][C:10]([O:13][C:14]2[CH:15]=[C:16]3[C:20](=[C:21]([O:23][CH:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[CH:22]=2)[NH:19][C:18]([C:30]2[S:31][CH:32]([CH2:35][C:36]([NH:41][CH3:45])=[O:37])[CH2:33][N:34]=2)=[CH:17]3)=[CH:9][CH:8]=1

Participants

10

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 6364545Methylamine hydrochlorideHCID 58081071HCID 58081071, compound

Product 1

HCID 66726198HCID 66726198, compoundYield 52.2%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of {2-[5-({6-[(2-methoxyethoxy)methyl]pyridin-3-yl}oxy)-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetic acid (157 mg) in N,N-dimethylformamide (5 mL) were added 1-hydroxybenzotriazole monohydrate (67 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (83 mg), methylamine hydrochloride (30 mg), and triethylamine (0.060 mL), and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained crude product was subjected to basic silica gel column chromatography (ethyl acetate:hexane=0:100 to 100:0, volume ratio) to give the title compound (84 mg, yield 52%) as a yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained crude product

Sources & evidence

ORD record
ord-c43582e335ca43ee90db8fe2fa340038
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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