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

HRID 1698085Notes

Reaction equation

HRID 1698085 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, 1H) 8.67 (d, 1H) 8.03 (dd, 1H) 7.75 (d, 1H) 7.35 (d, 1H) 6.93 (dd, 1H) 6.75 (d, 1H) 3.63 (q, 2H) 3.07 (s, 3H) 1.11 (t, 3H); MS m/z (M+H) 286.

Workup

  1. customRecrystallization from methanol

Sources & evidence

ORD record
ord-056692db0f854af89674b001fb40f1d8
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

Loading…