1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 86613974, compound

HRID 870080Notes

Reaction equation

HRID 870080 reaction equation
[C:1]1([CH2:7][S:8]([N:11]2[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([OH:20])=O)=[CH:12]2)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[O:44]1[CH2:49][CH2:48][CH2:47][CH2:46][CH:45]1[O:50][NH2:51]>CN(C)C=O.C(N(CC)CC)C>[C:1]1([CH2:7][S:8]([N:11]2[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([NH:51][O:50][CH:45]3[CH2:46][CH2:47][CH2:48][CH2:49][O:44]3)=[O:20])=[CH:12]2)(=[O:9])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 66646065(E)-3-(1-phenylmethanesulfonyl-1H-pyrrol-3-yl)-acrylic acid2×

Product 1

HCID 86613974HCID 86613974, compoundYield 47.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

0.295 g of (E)-3-(1-phenylmethansulfonyl-1H-pyrrol-3-yl)-acrylic acid (compound B1), 0.152 g of N-hydroxybenzotriazole hydrate (HOBt?H2O) and 561 μl of triethylamine are dissolved in 20 ml of N,N-dimethylformamide (DMF) at room temperature. Afterwards it is added 0.601 g of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC?HCl) and stirred for 1 hour at room temperature. Then is added 0.152 g of O-(tetrahydro-2H-pyran-2-yl)-hydroxylamine and stirred for 2 hour. The DMF is evaporated under high vacuo. Water is added and the mixture was extracted with ethyl acetate. The organic phase is dried over sodium sulfate. Then it is filtered and evaporated under vacuo. The crude product is purified by silica gel flash chromatography using a gradient of dichloromethane/methanol from 99:1 to 98:2 to give 0.189 g of the title compound as a pale grey solid.

Workup

  1. stirringstirred for 2 hour
  2. customThe DMF is evaporated under high vacuo
  3. additionWater is added
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. filtrationThen it is filtered
  7. customevaporated under vacuo
  8. customThe crude product is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-471662144a804ea491b8de2859c8ec99
Source dataset
uspto-grants-2015_03
Patent number
US08969401B2

Reaction notes

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