1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 130384741, compound

HRID 2284860Notes

Reaction equation

HRID 2284860 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:10]1[CH:11]=[C:12]([CH:23]=[CH:24][CH:25]=1)[O:13][CH2:14][C:15]1[O:16][CH:17]=[C:18]([C:20]([OH:22])=[O:21])[N:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:32][C:33]1[CH:34]=[N+:35]([O-:53])[CH:36]=[C:37]([Cl:52])[C:38]=1[CH2:39][C@@H:40]([C:42]1[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[C:44]([O:50][CH3:51])[CH:43]=1)O.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.CN(C1C=CN=CC=1)C>[Cl:52][C:37]1[CH:36]=[N+:35]([O-:53])[CH:34]=[C:33]([Cl:32])[C:38]=1[CH2:39][C@H:40]([O:21][C:20]([C:18]1[N:19]=[C:15]([CH2:14][O:13][C:12]2[CH:23]=[CH:24][CH:25]=[C:10]([C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:11]=2)[O:16][CH:17]=1)=[O:22])[C:42]1[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[C:44]([O:50][CH3:51])[CH:43]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 71092494(S)-3,5-dichloro-4-(2-(3,4-dimethoxyphenyl)-2-hydroxyethyl)pyridine 1-oxideHCID 118114356HCID 118114356, compound

Product 1

HCID 130384741HCID 130384741, compoundYield 36.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 2-[[3-[(S)-(tert-butoxycarbonylamino)-phenyl-methyl]phenoxy]methyl]oxazole-4-carboxylic acid (350 mg, 0.825 mmol) in DMF (12.3 mL) was added (1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethanol (284 mg, 0.825 mmol), DMAP (50.4 mg, 0.412 mmol) and EDC hydrochloride (316.2 mg, 1.65 mmol). The reaction was stirred at room temperature for 23 h. The majority of the DMF was removed in vacuo and the residue was partitioned between ethyl acetate (30 mL) and saturated aqueous NaHCO3 solution (30 mL). The aqueous phase was extracted twice with ethyl acetate (20 mL) and the combined organic phases were washed with brine, dried on MgSO4, filtered then concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-50% EtOAc in dichloromethane, to give the title compound (225.6 mg, 36%) as a colourless solid.

Workup

  1. customThe majority of the DMF was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate (30 mL) and saturated aqueous NaHCO3 solution (30 mL)
  3. extractionThe aqueous phase was extracted twice with ethyl acetate (20 mL)
  4. washthe combined organic phases were washed with brine
  5. customdried on MgSO4
  6. filtrationfiltered
  7. concentrationthen concentrated in vacuo
  8. customThe residue was purified via silica gel chromatography
  9. washeluting with 0-50% EtOAc in dichloromethane

Sources & evidence

ORD record
ord-c451307e3a70417ba115f419d8d9bf23
Source dataset
uspto-grants-2015_09
Patent number
US09145409B2

Reaction notes

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