1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 86730095, compound

HRID 523946Notes

Reaction equation

HRID 523946 reaction equation
[CH2:1]([CH:3]([CH2:39][CH3:40])[CH2:4][C:5]1([OH:38])[CH2:10][CH2:9][N:8]([C:11]([NH:13][C:14]2[CH:15]=[C:16]([CH:27]=[C:28]([O:30][C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[CH:29]=2)[O:17][C:18]2[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=2)=[O:12])[CH2:7][CH2:6]1)[CH3:2].[O:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH:42]1[O:47][NH2:48].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>CN(C=O)C.C(OCC)(=O)C.O>[CH2:39]([CH:3]([CH2:1][CH3:2])[CH2:4][C:5]1([OH:38])[CH2:10][CH2:9][N:8]([C:11]([NH:13][C:14]2[CH:15]=[C:16]([O:17][C:18]3[CH:26]=[CH:25][C:21]([C:22](=[O:23])[NH:48][O:47][CH:42]4[CH2:43][CH2:44][CH2:45][CH2:46][O:41]4)=[CH:20][CH:19]=3)[CH:27]=[C:28]([O:30][C:31]3[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=3)[CH:29]=2)=[O:12])[CH2:7][CH2:6]1)[CH3:40]

Participants

8

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 71547628HCID 71547628, compound

Product 1

HCID 86730095HCID 86730095, compoundYield 84.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound prepared in Example 9(1) (20 mg) was dissolved in DMF (200 μL), added with O-(tetrahydro-2H-pyran-2-yl)hydroxylamine (4.2 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) (19 mg) and 1-hydroxybenzotriazole monohydrate (HOBt) (15 mg) and stirred at room temperature for 24 hours. The reaction solution was diluted with ethyl acetate and added with water and the aqueous layer was extracted with MTBE. The organic layer was combined, washed with water, a saturated sodium hydrogen carbonate aqueous solution and a saturated ammonium chloride aqueous solution and then concentrated. The resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1) to give the titled compound (19.6 mg) having the following physical properties.

Workup

  1. extractionthe aqueous layer was extracted with MTBE
  2. washwashed with water
  3. concentrationa saturated sodium hydrogen carbonate aqueous solution and a saturated ammonium chloride aqueous solution and then concentrated
  4. customThe resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-6b238d458f49495588a49db9e108d351
Source dataset
uspto-grants-2016_05
Patent number
US09340499B2

Reaction notes

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