Benzaldehyde → (5-(Benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)(phenyl)methanol

HRID 1426179Notes

Reaction equation

HRID 1426179 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.[CH:31](=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.Cl>>[CH2:2]([O:9][C:10]1[CH:15]=[C:14]([CH:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[OH:38])[CH:13]=[N:12][C:11]=1[NH:17][C:18]1[S:19][CH:20]=[C:21]([CH3:23])[N:22]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 5

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 160614653-(benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochlorideHCID 178418339ButyllithiumHCID 178418348HCID 178418348, compound

Product 1

HCID 59225682(5-(Benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)(phenyl)methanolYield 48.5%

Procedure

3-(Benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine (Example 1; 0.350 g, 0.930 mmol), MeLi (0.727 ml, 1.16 mmol), butyllithium (0.465 ml, 1.16 mmol), and benzaldehyde (0.0987 g, 0.930 mmol) were reacted according to Example 7 to provide (5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)(phenyl)methanol (0.182 g, 48.5% yield) after HCl salt formation. 1H NMR (DMSO-d6) δ 7.94 (s, 1H), 7.58 (s, 1H), 7.55 (d, 2H), 7.40-7.28 (m, 7H), 7.22 (m, 1H), 6.81 (s, 1H), 5.75 (s, 1H), 5.29 (s, 2H), 2.30 (s, 3H). Mass spectrum (apci) m/z=404.1 (M+H-HCl).

Sources & evidence

ORD record
ord-3ce64e7582b7487ca07a7fb12ff369a4
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

Loading…