Dimethylformamide → HCID 16661007, compound

HRID 1426142Notes

Reaction equation

HRID 1426142 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][CH:13]=[C:14](Br)[CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Li]C.C([Li])CCC.CN(C)[CH:33]=[O:34]>>[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:13]=[C:14]([CH:15]=1)[CH:33]=[O:34])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 160614653-(benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochlorideHCID 178418339ButyllithiumHCID 178418348HCID 178418348, compound

Product 1

HCID 16661007HCID 16661007, compoundYield 75.2%

Procedure

3-(Benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine (prepared according to Example 1; 1.0 g, 2.66 mmol), MeLi (1.83 ml, 2.92 mmol), butyl lithium (1.17 ml, 2.92 mmol), and N,N-dimethylformamide (0.823 ml, 10.6 mmol) were reacted according to the method of Example 7 to provide the title compound (650 mg, 75.2% yield) as a pale yellow solid. 1H NMR (CDCl3) δ 9.91 (s, 1H), 8.88 (bs, 1H), 8.40 (d, 1H), 7.56 (d, 1H), 7.42 (m, 5H), 6.51 (m, 1H), 5.17 (s, 2H), 2.35 (s, 3H). Mass spectrum (apci) m/z=326.0 (M+H).

Sources & evidence

ORD record
ord-1e0fbe09b686463fbfb7d46855646016
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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