N-(4-Methoxybenzyl)thiazol-2-amine synthesis

96-50-4 Synthesis

96-50-4
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123-11-5 Synthesis

123-11-5
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384858-14-4
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Yield:384858-14-4 78%

Reaction Conditions:

Stage #1: 2-thiazolylamine;4-methoxy-benzaldehydewith triisopropoxytitanium(IV) chloride in dichloromethane; for 0.5 h;Inert atmosphere;
Stage #2: with sodium tris(acetoxy)borohydride in dichloromethane at 20; for 2 h;Inert atmosphere;

Steps:

N-(4-Methoxybenzyl)thiazol-2-amine (23)

To a stirred solution of thiazol-2-amine (14 ml, 160 mmol) and 4-methoxybenzaldehyde (18 ml, 15 mmol) in DCM (450 ml) was added TiCl(OiPr)₃ (77 ml, 320 mmol) slowly under argon atmosphere to yield a bright red solution. The solution was stirred for 30 minutes before the portion-wise addition of freshly ground NaBH(OAc)₃. The reaction mixture was stirred at room temperature for 2 hours and saturated aqueous NaHCO3was slowly poured into the reaction mixture until a pH of ~7 was obtained and a white precipitate was formed. The mixture was filtered through a pad of Celite and the filtrate was partitioned between water (100 mL) and DCM (200 mL). The layers were separated and the aqueous layer was extracted with DCM (100 mL). The organic layers were combined, dried over sodium sulfate and concentrated to yield a light yellow solid (contaminated with an impurity). The material was then triturated with DCM/MeOH and collected by vacuum filtration to yield N-(4-methoxybenzyl)thiazol-2-amine (25 g, 120 mmol, 78 % yield) as a light yellow solid. ¹H NMR (400 MHz, DMSO-d₆) δ 7.95 (t, J=5.67 Hz, 1H), 7.23-7.28 (m, 2H), 7.00 (d, J=3.62 Hz, 1H), 6.86-6.91 (m, 2H), 6.59 (d, J=3.62 Hz, 1H), 4.35 (s, 1H), 4.34 (s, 1H), 3.72 (s, 3H); m/z (ESI) 221.1 (M+H)+.

References:

La, Daniel S.;Peterson, Emily A.;Bode, Christiane;Boezio, Alessandro A.;Bregman, Howard;Chu-Moyer, Margaret Y.;Coats, James;DiMauro, Erin F.;Dineen, Thomas A.;Du, Bingfan;Gao, Hua;Graceffa, Russell;Gunaydin, Hakan;Guzman-Perez, Angel;Fremeau, Robert;Huang, Xin;Ilch, Christopher;Kornecook, Thomas J.;Kreiman, Charles;Ligutti, Joseph;Jasmine Lin, Min-Hwa;McDermott, Jeff S.;Marx, Isaac;Matson, David J.;McDonough, Stefan I.;Moyer, Bryan D.;Nho Nguyen, Hanh;Taborn, Kristin;Yu, Violeta;Weiss, Matthew M. [Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,# 15,p. 3477 - 3485] Location in patent:supporting information

2-Thiazolamine, N-[(4-methoxyphenyl)methylene]-

91207-44-2
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384858-14-4
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123-11-5 Synthesis

123-11-5
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384858-14-4
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303122-55-6
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100-07-2 Synthesis

100-07-2
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