Ethyl Acetate → 2-(3-Dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-ylamine

HRID 1174889Notes

Reaction equation

HRID 1174889 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:14][N:15]([CH3:21])[C@@H:16]1[CH2:20][CH2:19][NH:18][CH2:17]1.C(OCC)(=O)C>C1COCC1>[CH3:14][N:15]([CH3:21])[CH:16]1[CH2:20][CH2:19][N:18]([C:2]2[S:3][C:4]3[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:5]=3[N:6]=2)[CH2:17]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 754762-Chloro-6-nitrobenzothiazoleHCID 2758521(3R)-(+)-3-(Dimethylamino)pyrrolidine

Product 1

HCID 632315072-(3-Dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-ylamineYield 47.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Suspend 2-chloro-6-nitrobenzthiazole (8.49 g, 39.6 mmol) in THF (100 mL). Slowly add (3R)-(+)-3-(dimethylamino)pyrrolidine (5.24 g, 45.9 mmol). Stir the reaction overnight at room temperature. Dilute the reaction with ethyl acetate and then wash with water and brine. Concentrate the organic portion in vacuo, and triturate the resulting residue with MeOH to afford the title compound (4.94 g, 43%). 1H NMR (400 MHz, DMSO-d6): δ 8.81 (d, 1H, J=2.2 Hz), 8.14 (dd, 1H, J=9.0, 2.4 Hz), 7.52 (d, 1H, J=8.8 Hz), 4.00-3.43 (m, 3H), 3.30 (m, 1H), 2.91 (m, 1H), 2.20-2.15 (m, 7H), 1.93 (m, 1H).

Workup

  1. customthe reaction overnight at room temperature
  2. additionDilute
  3. washwash with water and brine
  4. concentrationConcentrate the organic portion in vacuo
  5. customtriturate the resulting residue with MeOH

Sources & evidence

ORD record
ord-f8eee019d223407b958aa5caadb8af55
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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