Ethanol → 2-(6-Methoxypyridin-3-yl)-1,3-benzothiazol-6-amine

HRID 1851758Notes

Reaction equation

F[C:2]1[N:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15](OC)[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[NH2:19]CC1C=NC=CC=1.[CH2:27]([OH:29])C>O>[CH3:27][O:29][C:2]1[N:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([NH2:19])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-(6-fluoropyridin-3-yl)-6-methoxy-1,3-benzothiazole (0.10 g, 0.38 mmol) and 3-(aminomethyl)pyridine (1.0 mL, 9.5 mmol) in ethanol (4 mL) was heated at 100° C. for 9 minutes in a microwave reactor. The mixture was diluted with water, then cooled to r.t. and the formed precipitate was collected by filtration and dried. The crude product was purified by prep. HPLC to give the title compound (71 mg) as a solid. 1H NMR (CHLOROFORM-d) δ 8.75 (d, 1 H) 8.66 (d, 1 H) 8.56 (dd, 1 H) 8.11 (dd, 1 H) 7.89 (d, 1H) 7.66-7.76 (m, 1 H) 7.34 (d, 1 H) 7.26-7.31 (m, 2 H) 7.07 (dd, 1 H) 6.50 (d, 1 H) 5.18 (t, 1 H) 4.67 (d, 2 H) 3.90 (s, 3 H); MS m/z (M+H) 348.9.

Workup

temperaturecooled to r.t.
filtrationthe formed precipitate was collected by filtration
customdried
customThe crude product was purified by prep

Sources & evidence

ORD record: ord-6e1c7ba719d042bf84d8637c89fe7393
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957215B2

Reaction notes

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