M-Phenylenediamine → HCID 90052166, compound

HRID 2284645Notes

Reaction equation

HRID 2284645 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[C:38]1([NH2:45])[CH:43]=[CH:42][CH:41]=[C:40]([NH2:44])[CH:39]=1.C(=O)([O-])O.[Na+]>CN(C)C=O.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>[NH2:44][C:40]1[CH:39]=[C:38]([NH:45][C:10](=[O:12])[C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])([CH3:14])[CH3:13])[CH:43]=[CH:42][CH:41]=1

Participants

9

Reactant 5

HCID 7935M-PhenylenediamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanineHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 90052166HCID 90052166, compoundYield 66.5%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of 2-(tert-butoxycarbonylamino)isobutyric acid (203 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (211 mg) and 1-hydroxybenzotriazole monohydrate (149 mg) in N,N-dimethylformamide (3 mL), N,N-diisopropylethylamine (510 μL) was added at room temperature, and the mixture was stirred at the same temperature for 1 hour and 30 minutes. To the reaction mixture, a solution of 1,3-phenylenediamine (260 mg) in N,N-dimethylformamide (2 mL) was added at room temperature, and the mixture was stirred at 80° C. for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature, and then saturated aqueous sodium hydrogencarbonate and ethyl acetate were added to the mixture. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain tert-butyl (1-((3-aminophenyl)amino)-2-methyl-1-oxopropan-2-yl)carbamate (B8, 195 mg) as white solid.

Workup

  1. stirringthe mixture was stirred at 80° C. for 1 hour and 30 minutes
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5e97f68985a44776aed6276bcbb26389
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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