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5-methyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-2-(2-nitrophenyl)-6-phenyl-1,3-benzoxazole-4-carbonitrile → HCID 68584840, compound

HRID 17503
Notes
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Reaction equation

HRID 17503 reaction equation
[CH3:1][C:2]1[C:19]([C:20]#[N:21])=[C:6]2[N:7]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N+:16]([O-])=O)[O:9][C:5]2=[C:4]([N:22]2[CH2:26][CH2:25][C@H:24]([N:27]([CH3:29])[CH3:28])[CH2:23]2)[C:3]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[H][H]>[C].[Pd].C(OCC)(=O)C>[NH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:8]1[O:9][C:5]2[C:6](=[C:19]([C:20]#[N:21])[C:2]([CH3:1])=[C:3]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:4]=2[N:22]2[CH2:26][CH2:25][C@H:24]([N:27]([CH3:28])[CH3:29])[CH2:23]2)[N:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 685855645-methyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-2-(2-nitrophenyl)-6-phenyl-1,3-benzoxazole-4-carbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 68584840HCID 68584840, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst
HCID 8857
Ethyl Acetate
Solvent

Procedure

10% Palladium-carbon (150 mg) was added to an ethyl acetate (30 ml) solution of 5-methyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-2-(2-nitrophenyl)-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-211) (128 mg, 0.27 mmol), followed by stirring at the same temperature under atmospheric pressure of hydrogen for 1.5 hours. The catalyst was removed by filtration with washing with ethyl acetate, the filtrate was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography. Elution with a mixed solvent of chloroform/methanol (99:1→96:4, v/v) gave the entitled compound (65 mg, 55%) as a pale yellow solid.

Workup

  1. customThe catalyst was removed by filtration
  2. washwith washing with ethyl acetate
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washElution with a mixed solvent of chloroform/methanol (99:1→96:4, v/v)

Sources & evidence

ORD record
ord-75d04971662d43ed8bc1ff1fda97adc2
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737166B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes