Tetrahydrofuran → HCID 71201916, compound

HRID 1908674Notes

Reaction equation

HRID 1908674 reaction equation
Cl.CN(C)CCCN=C=NCC.ON1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2N=N1.Cl.[CH3:24][C:25]1[CH:26]=[CH:27][C:28]([C@@H:31]([NH2:33])[CH3:32])=[N:29][CH:30]=1.C(N(CC)C(C)C)(C)C.[CH2:43]1[CH2:47][O:46][CH2:45][CH2:44]1>O>[CH3:24][C:25]1[CH:26]=[CH:27][C:28]([C@@H:31]([NH:33][C:45]([C@H:44]2[CH2:43][C@@H:47]2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:46])[CH3:32])=[N:29][CH:30]=1

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86675613HCID 86675613, compound

Product 1

HCID 71201916HCID 71201916, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.709 g, 3.70 mmol) and 1-hydroxybenzotriazole (0.667 g, 4.93 mmol) were added to a stirred mixture of IM46 (0.60 g, 3.70 mmol) and commercially available (S)-1-(5-methyl-pyridin-2-yl)-ethylamine hydrochloride (Supplier Netchem Inc., Catalog No 528193) (0.426 g, 2.47 mmol) and N,N-diisopropylethylamine (0.859 ml, 4.93 mmol) in THF (25 ml). The solution was stirred at rt overnight. Water was added and the mixture was extracted with EtOAc (3×80 ml). The combined organic phases were washed with brine, dried over MgSO4, filtered and the solvent was evaporated of in vac. The crude product was purified by silica gel chromatography (EtOAc in heptanes 1:1). Yield of Compound 2: 110 mg (16%). LC-MS (m/z) 281.1 (MH+), tR=0.91 min (method A).

Workup

  1. extractionthe mixture was extracted with EtOAc (3×80 ml)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was evaporated of in vac
  6. customThe crude product was purified by silica gel chromatography (EtOAc in heptanes 1:1)

Sources & evidence

ORD record
ord-dd944e7c7523447283b0a27378df89b8
Source dataset
uspto-grants-2013_12
Patent number
US08598213B2

Reaction notes

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