5-METHYL-4,5,6,7-TETRAHYDRO[1,3]THIAZOLO[5,4-C]PYRIDIN-2-AMINE synthesis
- Product Name:5-METHYL-4,5,6,7-TETRAHYDRO[1,3]THIAZOLO[5,4-C]PYRIDIN-2-AMINE
- CAS Number:17899-48-8
- Molecular formula:C7H11N3S
- Molecular Weight:169.25
1445-73-4
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420-04-2
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17899-48-8
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Yield: 78%
Reaction Conditions:
with pyrrolidine;sulfur in isopropyl alcohol at 50; for 2 h;
Steps:
1 Reference Example 1; 2-Amino-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine (1-n) (method described in International Patent Publication No. WO 2005/047296)
2-Amino-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine (1-n) (method described in International Patent Publication No. WO 2005/047296)
To a solution of 1-methyl-4-piperidone (180.0 g) in 2-PrOH (1.44 L) heated to 50° C., a solution of cyanamide (67.0 g) in 2-PrOH (360 mL), and a sulfur powder (51.0 g) were added.
To the reaction mixture, pyrrolidine (13.3 mL) was added, and the mixture was stirred at 50° C. for 2 hours, then left to cool to room temperature, and stirred overnight.
The reaction mixture was cooled to 10° C. or lower in an ice water bath and stirred at the same temperature as above for 1 hour.
The deposited crystals were filtered, washed with 2-PrOH (540 mL), and then dried under reduced pressure at 40° C. to obtain the title compound (209.9 g, 78%).
1H-NMR (CDCl3) δ ppm: 4.86 (br, 2H), 3.47-3.46 (t, 2H, J=1.9 Hz), 2.78-2.71 (m, 2H), 2.71-2.65 (m, 2H), 2.47 (s, 3H).
MS(FAB) m/z: 170 (M+H)+
References:
Daiichi Sankyo Company, Limited;UEDA, Tsuyoshi US2017/50983, 2017, A1 Location in patent:Paragraph 0126; 0127; 0128; 0129; 0130; 0131; 0132; 0133
123-75-1
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1445-73-4
467 suppliers
$15.00/25g
17899-48-8
91 suppliers
$80.00/250mg