N'-Hydroxybenzenecarboximidamide → HCID 70576578, compound

HRID 1477834Notes

Reaction equation

HRID 1477834 reaction equation
[OH:1][N:2]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[NH2:4].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([N:22]2[C:30]3[C:25](=[C:26]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])[CH:27]=[CH:28][CH:29]=3)[CH:24]=[CH:23]2)[C:19](O)=O)=[CH:14][CH:13]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([C:19]2[O:1][N:2]=[C:3]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:4]=2)[N:22]2[C:30]3[C:25](=[C:26]([NH:31][S:32]([CH3:35])(=[O:33])=[O:34])[CH:27]=[CH:28][CH:29]=3)[CH:24]=[CH:23]2)=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 69186N'-HydroxybenzenecarboximidamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 70564863HCID 70564863, compound

Product 1

HCID 70576578HCID 70576578, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N′-Hydroxybenzenecarboximidamide (49 mg, 0.36 mmol) was added to a stirred solution of compound 6a (90 mg, 0.24 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (91 mg, 0.48 mmol), 1-hydroxybenzotriazole (44 mg, 0.29 mmol) and N,N,-diisopropylethylamine (50 μL, 0.29 mmol) in DMF (2.4 mL). The reaction was allowed to stir at rt for 2 h, at which time, the reaction was partitioned between ethyl acetate and water. The layers were separated, and the organic layer was washed with water and brine, dried over MgSO4, filtered and concentrated to a crude oil that was dissolved in toluene (2.0 mL). The resulting mixture was heated to 100° C. for 1 h, at which time, the reaction was concentrated in vacuo, and the resulting crude residue was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (CH3CN/H2O as eluent, 0.05% TFA as modifier), followed by lyophilization of the purified fractions to afford the title compound 63. m/z (ES) 479 (MH)+; IP=C rating.

Workup

  1. customthe reaction was partitioned between ethyl acetate and water
  2. customThe layers were separated
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to a crude oil that
  7. dissolutionwas dissolved in toluene (2.0 mL)
  8. temperatureThe resulting mixture was heated to 100° C. for 1 h, at which time
  9. concentrationthe reaction was concentrated in vacuo
  10. customthe resulting crude residue was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (CH3CN/H2O as eluent, 0.05% TFA as modifier)

Sources & evidence

ORD record
ord-20e7b7dbdb8c4bb2b7758312d97db8dc
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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