N-Methylethylamine → N-ethyl-5-(6-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

HRID 1698084Notes

Reaction equation

HRID 1698084 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.[CH2:19]([NH:21][CH3:22])[CH3:20]>O>[CH2:19]([N:21]([CH3:22])[C:2]1[CH:3]=[CH:4][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:6][N:7]=1)[CH3:20]

Participants

4

Reactant 2

HCID 12219N-MethylethylamineHCID 248037222-(6-Fluoropyridin-3-yl)-6-methoxy-1,3-benzothiazole

Product 1

HCID 24803889N-ethyl-5-(6-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

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, 0.289 mmol), water (2.0 ml-L) and ethylmethylamine (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 dried in a desicator over P2O5 to yield the product (70 mg) as a beige solid. 1H NMR δ ppm 8.71 (d, 1H) 8.06 (dd, 2.53 Hz, 1H) 7.85 (d, 1H) 7.66 (d, 1H) 7.08 (dd, 1H) 6.76 (d, 1H) 3.84 (s, 3H) 3.64 (q, 2H) 3.08 (s, 3H) 1.12 (t, 3H); MS m/z (M+H) 300.

Workup

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

Sources & evidence

ORD record
ord-400e8f56670140f68d4e9edc2bdc708f
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

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