Hexachloroethane → 3-(benzyloxy)-5-chloro-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride

HRID 1426094Notes

Reaction equation

Cl.[CH2:2]([O:9][C:10]1[C:11]([NH:17][C:18]2[S:19][CH:20]=[C:21]([CH3:23])[N:22]=2)=[N:12]C=C(Br)[CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Li]C.C([Li])CCC.[Cl:31][C:32]([Cl:38])(Cl)[C:33](Cl)(Cl)Cl>>[ClH:31].[CH2:2]([O:9][C:10]1[C:11]([NH:17][C:18]2[S:19][CH:20]=[C:21]([CH3:23])[N:22]=2)=[N:12][CH:33]=[C:32]([Cl:38])[CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Reactant 4

HCID 6214Hexachloroethane

HCID 160614653-(benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride

HCID 178418339Butyllithium

HCID 178418348HCID 178418348, compound

Product 1

HCID 727028703-(benzyloxy)-5-chloro-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochlorideYield 30.2%

Procedure

3-(Benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine (prepared according to Example 1; 0.225 g, 0.598 mmol), MeLi (0.467 mL, 0.747 mmol), butyllithium (0.299 mL, 0.747 mmol), and perchloroethane (0.991 g, 4.19 mmol) were reacted according to the method of Example 7 to provide 3-(benzyloxy)-5-chloro-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride (0.060 g, 30.2% yield). 1H NMR (CDCl3) δ 12.43 (bs, 1H), 7.91 (d, 1H), 7.59 (m, 2H), 7.41 (m, 2H), 7.33 (m, 1H), 7.20 (d, 1H), 6.41 (s, 1H), 5.36 (s, 2H), 2.47 (s, 3H). Mass spectrum (apci) m/z=332.1 (M+H-HCl).

Sources & evidence

ORD record: ord-ee7f59c34e1c4274b337d849aeeb7913
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933077B2

Reaction notes

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