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

HRID 1851766Notes

Reaction equation

HRID 1851766 reaction equation
C([N:3]([CH3:21])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]3[CH:18]=[C:17](OC)[CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:6][N:5]=1)C.C(NC1N=CC(C2SC3C=[C:38]([OH:40])C=CC=3N=2)=CC=1)C>>[CH3:38][O:40][C:16]1[CH:17]=[CH:18][C:12]2[S:11][C:10]([C:7]3[CH:8]=[CH:9][C:4]([NH:3][CH3:21])=[N:5][CH:6]=3)=[N:14][C:13]=2[CH:15]=1

Participants

3

Reactant 2

HCID 248038882-[6-(Ethylamino)pyridin-3-yl]-1,3-benzothiazol-6-olHCID 24803889N-ethyl-5-(6-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

Product 1

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

Procedure

N-Ethyl-5-(6-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine (55.4 mg, 0.185 mmol) was subjected to the procedure described for 2-[6-(ethylamino)pyridin-3-yl]-1,3-benzothiazol-6-ol. Recrystallization from methanol gave 23.7 mg of the title compound as a pale yellow solid. 1H NMR δ ppm 9.75 (s, 1 H) 8.67 (d, 1 H) 8.03 (dd, 1 H) 7.75 (d, 1 H) 7.35 (d, 1 H) 6.93 (dd, 1 H) 6.75 (d, 1 H) 3.63 (q, 2 H) 3.07 (s, 3 H) 1.11 (t, 3 H); MS m/z (M+H) 286.

Workup

  1. customRecrystallization from methanol

Sources & evidence

ORD record
ord-809d716cb79f426caaa698b5dc5fb8e5
Source dataset
uspto-grants-2015_02
Patent number
US08957215B2

Reaction notes

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