Dimethyl-[1-(5-nitro-benzooxazol-2-yl)-pyrrolidin-3-yl]-amine → 2-(3-Dimethylamino-pyrrolidin-1-yl)-benzooxazol-5-ylamine

HRID 1174918Notes

Reaction equation

HRID 1174918 reaction equation
[CH3:1][N:2]([CH3:20])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][C:11]=3[N:12]=2)[CH2:4]1>C(O)(=O)C.O>[CH3:1][N:2]([CH3:20])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:11]=3[N:12]=2)[CH2:4]1

Participants

4

Reactant 1

HCID 68773862Dimethyl-[1-(5-nitro-benzooxazol-2-yl)-pyrrolidin-3-yl]-amine

Product 1

HCID 687717302-(3-Dimethylamino-pyrrolidin-1-yl)-benzooxazol-5-ylamineYield 86.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Combine dimethyl-[1-(5-nitro-benzooxazol-2-yl)-pyrrolidin-3-yl]-amine (1.00 g, 3.62 mmol) and Fe0 (1.98 g, 35.4 mmol) in acetic acid (20 mL) and stir at 40° C. for 2 h. Dilute with water (50 mL) and filter through Celite®. Wash with copious amounts of water and MeOH. Make the filtrate alkaline with 5 N NaOH and extract twice with CH2Cl2 (2×). Concentrate in vacuo to afford the title compound (769 mg, 86%). 1H NMR (400 MHz, CDCl3): δ 7.00 (d, 1H, J=8.4 Hz), 6.70 (d, 1H, J=2.2 Hz), 6.32 (dd, 1H, J=8.4, 2.6 Hz), 3.88 (dd, 1H, J=9.9, 7.1 Hz), 3.81 (m, 1H), 3.62-3.50 (m, 3H), 3.39 (dd, 1H, J=10.1, 8.8 Hz), 2.83 (m, 1H), 2.30 (s, 6H), 2.21 (m, 1H), 1.93 (m, 1H).

Workup

  1. filtrationfilter through Celite®
  2. washWash with copious amounts of water and MeOH
  3. extractionextract twice with CH2Cl2 (2×)
  4. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-9b59d9176f6f4be8b11d7d8b6154410f
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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