Dimethylamine → 5-(6-methoxybenzo[d]thiazol-2-yl)-N,N-dimethylpyridin-2-amine

HRID 1698079Notes

Reaction equation

HRID 1698079 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.[CH3:19][NH:20][CH3:21].O>C1COCC1>[CH3:18][O:17][C:15]1[CH:14]=[CH:13][C:11]2[N:12]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([N:20]([CH3:21])[CH3:19])=[N:7][CH:6]=3)[S:9][C:10]=2[CH:16]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 248037222-(6-Fluoropyridin-3-yl)-6-methoxy-1,3-benzothiazole

Product 1

HCID 247578785-(6-methoxybenzo[d]thiazol-2-yl)-N,N-dimethylpyridin-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(6-Fluoropyridin-3-yl)-6-methoxy-1,3-benzothiazole (0.201 g) and 2 M dimethylamine in THF (5 mL) were heated in a microwave oven at 100° C. for 5 min. Water was added and the precipitated product was filtered off, washed with water and dried in a desicator over P2O5 to yield 0.193 g of the product as a pale beige solid. 1H NMR δ ppm 8.71 (d, 1H) 8.07 (dd, 1H) 7.84 (d, 1H) 7.65 (d, 1H) 7.08 (dd, 1H) 6.77 (d, 1H) 3.84 (s, 3H) 3.12 (s, 6H); MS m/z (M+H) 286.

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-4dfc50585fc44dcfa69d33174d771a37
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

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