Benzothiazol-5-amine → 5-(5-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

HRID 1851762Notes

Reaction equation

HRID 1851762 reaction equation
[CH3:1][O:2]C1N=CC(C2SC3C=CC=CC=3N=2)=CN=1.[S:18]1[C:22]2[CH:23]=[CH:24][C:25](N)=[CH:26][C:21]=2[N:20]=[CH:19]1.Br[C:29]1[CH:30]=[CH:31][C:32]([NH:35][CH3:36])=[N:33][CH:34]=1>>[CH3:1][O:2][C:25]1[CH:24]=[CH:23][C:22]2[S:18][C:19]([C:29]3[CH:30]=[CH:31][C:32]([NH:35][CH3:36])=[N:33][CH:34]=3)=[N:20][C:21]=2[CH:26]=1

Participants

4

Reactant 3

HCID 70749Benzothiazol-5-amineHCID 156456635-Bromo-N-methylpyridin-2-amineHCID 248037262-(2-Methoxypyrimidin-5-yl)-1,3-benzothiazole

Product 1

HCID 248037275-(5-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

Procedure

The title compound was prepared according to the method used for the preparation of 2-(2-methoxypyrimidin-5-yl)-1,3-benzothiazole, now starting from 1,3-benzothiazol-5-amine (50 mg, 0.33 mmol) and 5-bromo-N-methylpyridin-2-amine (75 mg, 0.40 mmol). The crude material was purified on a preparative HPLC to give the title compound (12 mg) as a pale beige solid. 1H NMR δ ppm 8.62 (d, 1 H) 7.95 (dd, 1 H) 7.61 (d, 1 H) 7.19 (q, 1 H) 7.07 (d, 1 H) 6.69 (dd, 1 H) 6.56 (d, 1 H) 5.24 (s, 2 H) 2.85 (d, 3 H); MS m/z (M+H) 257.

Workup

  1. customThe title compound was prepared
  2. customThe crude material was purified on a preparative HPLC

Sources & evidence

ORD record
ord-28769d567c3344cf858f94a9f1481b1b
Source dataset
uspto-grants-2015_02
Patent number
US08957215B2

Reaction notes

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