Rac-methyl-(1-methyl-pyrrolidin-3-ylmethyl)-(5-nitro-benzooxazol-2-yl)-amine → Rac-n2-methyl-n2-(1-methyl-pyrrolidin-3-ylmethyl)-benzooxazole-2,5-diamine

HRID 1174925Notes

Reaction equation

[CH3:1][N:2]([CH2:15][CH:16]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17]1)[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:6]=2[N:7]=1>C(O)(=O)C.[Fe]>[CH3:1][N:2]([CH2:15][CH:16]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17]1)[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:6]=2[N:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Dissolve rac-methyl-(1-methyl-pyrrolidin-3-ylmethyl)-(5-nitro-benzooxazol-2-yl)-amine (1.48 g, 5.09 mmol) in acetic acid (90 mL) and add Fe (1.42 g, 25.4 mmol) to the solution. Stir the mixture at 40° C. for 3 h. Filter the reaction mixture through Celite® and wash with H2O/MeOH. Concentrate the reaction mixture in vacuo. Subject the residue to silica gel flash column chromatography (120 g column, 10% 2N NH3 in MeOH/CH2Cl2) to yield the desired product (0.913 g, 69%). mass spectrum (m/e): 261.2 (M+1).

Workup

filtrationFilter the reaction mixture through Celite®
washwash with H2O/MeOH
concentrationConcentrate the reaction mixture in vacuo

Sources & evidence

ORD record: ord-dac86a7540e2423b943f41b3f8724e08
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07838543B2

Reaction notes

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