2-tert-butyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-(3-nitrophenyl)-1,3-benzoxazole-4-carbonitrile → 6-(3-aminophenyl)-2-tert-butyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-1,3-benzoxazole-4-carbonitrile

HRID 17281

Reaction equation

HRID 17281 reaction equation
[C:1]([C:5]1[O:6][C:7]2[C:8](=[C:10]([C:32]#[N:33])[C:11]([CH3:31])=[C:12]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-])=O)[CH:23]=3)[C:13]=2[N:14]2[CH2:18][CH2:17][C@H:16]([N:19]([CH3:21])[CH3:20])[CH2:15]2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2]>Cl>[NH2:28][C:24]1[CH:23]=[C:22]([C:12]2[C:13]([N:14]3[CH2:18][CH2:17][C@H:16]([N:19]([CH3:20])[CH3:21])[CH2:15]3)=[C:7]3[O:6][C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])=[N:9][C:8]3=[C:10]([C:32]#[N:33])[C:11]=2[CH3:31])[CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 1

HCID 685844192-tert-butyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-(3-nitrophenyl)-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 685852886-(3-aminophenyl)-2-tert-butyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-1,3-benzoxazole-4-carbonitrileYield 17.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2-tert-Butyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-(3-nitrophenyl)-1,3-benzoxazole-4-carbonitrile (I-22) (30.7 mg, 68.6 μmol) was dissolved in 4 N hydrogen chloride (ethyl acetate solution, 2 ml) and the solvent was concentrated under reduced pressure. The residue was dissolved in methanol (8 ml), followed by catalytic hydrogenation at room temperature under normal pressure for 3 hours in the presence of 5% palladium-carbon (50% wet, 30 mg). The catalyst was separated by filtration, the filtrate was concentrated under reduced pressure, aqueous 10% sodium carbonate solution and ethyl acetate were added to the residue followed by stirring. The organic layer was collected by liquid-liquid separation, concentrated and purified by preparative TLC (developing solvent, chloroform:methanol=10:1) to obtain the entitled compound (4.9 mg) as a brown solid.

Workup

  1. concentrationthe solvent was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (8 ml)
  3. customThe catalyst was separated by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure, aqueous 10% sodium carbonate solution and ethyl acetate
  5. additionwere added to the residue
  6. customThe organic layer was collected by liquid-liquid separation
  7. concentrationconcentrated
  8. custompurified by preparative TLC (developing solvent, chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-86a44a0b379545d8b8b65129dc61708d
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Linked notes

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