Pyridine → HCID 17194044, compound

HRID 1601024Notes

Reaction equation

HRID 1601024 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[CH3:22][CH:23]([CH3:28])[CH2:24][C:25](Cl)=[O:26]>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:25](=[O:26])[CH2:24][CH:23]([CH3:28])[CH3:22])=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 1049PyridineHCID 66054Isovaleryl chlorideHCID 688611tert-Butyl (4-aminophenyl)carbamate

Product 1

HCID 17194044HCID 17194044, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of N-t-butoxycarbonyl-1,4-phenylene diamine (0.2 g) in dry tetrahydrofuran (20 ml) were added pyridine (0.15 ml) and 3-methylbutyryl chloride (0.13 g) and the reaction mixture was stirred for 1 hrs. The solution was diluted with ethyl acetate (50 ml), washed with a 3 N solution of hydrochloric acid (30 ml) and brine (30 ml), dried and concentrated in vacuum to give the title compound (0.27 g). T.l.c. cyclohexane/ethyl acetate 1/1, Rf =0.71.

Workup

  1. washwashed with a 3 N solution of hydrochloric acid (30 ml) and brine (30 ml)
  2. customdried
  3. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-3c35de54926f4cdaabb6fb4ff220cd93
Source dataset
uspto-grants-1999_11
Patent number
US05977136

Reaction notes

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