1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 71493624, compound

HRID 1469870Notes

Reaction equation

HRID 1469870 reaction equation
O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH:24]1([C:27]([C:29]2[CH:53]=[CH:52][C:32]([O:33][C@@H:34]([C:37]3[O:41][N:40]=[C:39]([C:42]4[CH:50]=[CH:49][C:45]([C:46](O)=[O:47])=[C:44]([F:51])[CH:43]=4)[N:38]=3)[CH2:35][CH3:36])=[CH:31][CH:30]=2)=[O:28])[CH2:26][CH2:25]1.[NH2:54][C@H:55]1[C@H:59]([OH:60])[CH2:58][O:57][C:56]1=[O:61]>C(OCC)(=O)C.O.CN(C)C=O>[CH:24]1([C:27]([C:29]2[CH:30]=[CH:31][C:32]([O:33][C@@H:34]([C:37]3[O:41][N:40]=[C:39]([C:42]4[CH:50]=[CH:49][C:45]([C:46]([NH:54][C@H:55]5[C@H:59]([OH:60])[CH2:58][O:57][C:56]5=[O:61])=[O:47])=[C:44]([F:51])[CH:43]=4)[N:38]=3)[CH2:35][CH3:36])=[CH:52][CH:53]=2)=[O:28])[CH2:25][CH2:26]1

Participants

8

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 53979006HCID 53979006, compoundHCID 89752807HCID 89752807, compound

Product 1

HCID 71493624HCID 71493624, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1-Hydroxybenzotriazole monohydrate (46.1 mg, 0.301 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (57.7 mg, 0.301 mmol) were added to an N,N-dimethylformamide (0.5 mL) solution of the 4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluorobenzoic acid synthesized in Reference Example 8 (103 mg, 0.252 mmol) at room temperature, and the mixture was stirred at the same temperature for 30 minutes. Subsequently, an N,N-dimethylformamide (1.0 mL) solution of the (3S,4S)-3-amino-4-hydroxydihydrofuran-2-(3H)-one synthesized in Reference Example 13 (44.2 mg) was added, and the mixture was further stirred at the same temperature for 30 minutes. Water was added to the reaction mixture, and the mixture was subjected to extraction twice with ethyl acetate. The organic layer thus obtained was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine, and then was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=70:30→30:70, v/v) to give the title compound (48.5 mg, yield: 38%).

Workup

  1. additionwas added
  2. stirringthe mixture was further stirred at the same temperature for 30 minutes
  3. extractionthe mixture was subjected to extraction twice with ethyl acetate
  4. customThe organic layer thus obtained
  5. washwas washed with a saturated aqueous solution of sodium hydrogen carbonate and brine
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-b2404019bb604e6bbb1f85006b29ac22
Source dataset
uspto-grants-2015_04
Patent number
US09006273B2

Reaction notes

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