Pyrrolidine → 6-Methoxy-2-(6-pyrrolidin-1-ylpyridin-3-yl)-1,3-benzothiazole

HRID 1698105Notes

Reaction equation

HRID 1698105 reaction equation
F[C:2]1[N:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>O>[CH3:18][O:17][C:15]1[CH:14]=[CH:13][C:11]2[N:12]=[C:8]([C:5]3[CH:6]=[N:7][C:2]([N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[CH:3][CH:4]=3)[S:9][C:10]=2[CH:16]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 248037222-(6-Fluoropyridin-3-yl)-6-methoxy-1,3-benzothiazole

Product 1

HCID 248044016-Methoxy-2-(6-pyrrolidin-1-ylpyridin-3-yl)-1,3-benzothiazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

In a microwave vial were added 2-(6-fluoropyridin-3-yl)-6-methoxy-1,3-benzothiazole (75 mg, 0.29 mmol), water (2.5 mL) and pyrrolidine (0.50 mL) and the reaction was heated in a microwave oven at 100° C. for 5 min. The precipitated product was filtered off, washed with water and methanol and dried in a desicator over P2O5 to give the title compound (76 mg) as a white solid. 1H NMR (CHLOROFORM-d) δ 8.77 (d, 1H) 8.13 (dd, 1H) 7.87 (d, 1H) 7.33 (d, 1H) 7.05 (dd, 1H) 6.44 (d, 1H) 3.89 (s, 3H) 3.63-3.46 (m, 4H) 2.11-1.98 (m, 4H); MS m/z (M+H) 312.

Workup

  1. filtrationThe precipitated product was filtered off
  2. washwashed with water and methanol
  3. dry with materialdried in a desicator over P2O5

Sources & evidence

ORD record
ord-2e0135ed21704bf1b78f809507a49b4d
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

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