2-[6-(methylamino)pyridin-3-yl]-1,3-benzothiazol-6-ol → 5-(5-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

HRID 1851772Notes

Reaction equation

HRID 1851772 reaction equation
[CH3:1][O:2]C1C=CC2N=C(C3C=CC(N)=NC=3)SC=2C=1.[CH3:19][NH:20][C:21]1[N:26]=[CH:25][C:24]([C:27]2[S:28][C:29]3[CH:35]=[C:34](O)[CH:33]=[CH:32][C:30]=3[N:31]=2)=[CH:23][CH:22]=1>>[CH3:1][O:2][C:33]1[CH:34]=[CH:35][C:29]2[S:28][C:27]([C:24]3[CH:23]=[CH:22][C:21]([NH:20][CH3:19])=[N:26][CH:25]=3)=[N:31][C:30]=2[CH:32]=1

Participants

3

Reactant 2

HCID 166632752-[6-(methylamino)pyridin-3-yl]-1,3-benzothiazol-6-olHCID 24756573HCID 24756573, compound

Product 1

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

Procedure

5-(6-Methoxy-1,3-benzothiazol-2-yl)pyridin-2-amine (190 mg, 0.74 mmol) was exposed to the procedure used for the preparation of 2-[6-(methylamino)pyridin-3-yl]-1,3-benzothiazol-6-ol. After neutralization, the precipitate was filtered off and washed with water. The crude solid was slurred in hot EtOAc/MeOH 95:5 and filtered. The filtrate was concentrated under reduced pressure and the residue was subjected to flash chromatography (EtOAc/MeOH 95:5) to give a product that was chromatographed once more (DCM/MeOH 95:5) to yield the title compound (65 mg). 1H NMR δ 9.74 (s, 1 H) 8.53 (d, 1 H) 7.93 (dd, 1 H) 7.73 (d, 1 H) 7.35 (d, 1 H) 6.93 (dd, 1 H) 6.61 (br s, 2 H) 6.55 (d, 1 H); MS ink (M+H) 244.

Workup

  1. filtrationAfter neutralization, the precipitate was filtered off
  2. washwashed with water
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto give a product that
  6. customwas chromatographed once more (DCM/MeOH 95:5)

Sources & evidence

ORD record
ord-04603feacf4343f4be66d1ccd934b0c7
Source dataset
uspto-grants-2015_02
Patent number
US08957215B2

Reaction notes

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