| Identification | More | [Name]
2-AMINO-4,7-DIHYDRO-5H-THIENO[2,3-C]PYRIDINE-3,6-DICARBOXYLIC ACID 6-TERT BUTYL ESTER 3-ETHYL ESTER | [CAS]
193537-14-3 | [Synonyms]
2-AMINO-4,7-DIHYDRO-5H-THIENO[2,3-C]PYRIDINE-3,6-DICARBOXYLIC ACID 6-TERT BUTYL ESTER 3-ETHYL ESTER
6-TERT-BUTYL 3-ETHYL-2-AMINO-4,5-DIHYDRO-THIENO[2,3-C]PYRIDINE-3,6(7H)-DICARBOXYLATE
6-(TERT-BUTYL) 3-ETHYL 2-AMINO-4,7-DIHYDROTHIENO[2,3-C]PYRIDINE-3,6(5H)-DICARBOXYLATE
BUTTPARK 75\08-01
Ethyl 2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate, N-BOC protected
Ethyl 2-amino-6-tertbutoxycarbonyl-4,5,6,7-tetrahydrothieno[2.3-c]pyridine-3-carboxylate
Thieno[2,3-c]pyridine-3,6(5H)-dicarboxylic acid, 2-amino-4,7-dihydro-, 6-(1,1-dimethylethyl) 3-ethyl ester
2-AMINO-6-BOC-4,5,6,7-TETRAHYDRO-THIENO[2,3-C]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER
BOC-ETHYL 2-AMINO-4,5,6,7-TETRAHYDROTHIENO[2,3-C]PYRIDINE-3-CARBOXYLATE | [EINECS(EC#)]
251-156-6 | [Molecular Formula]
C15H22N2O4S | [MDL Number]
MFCD05664039 | [Molecular Weight]
326.41 | [MOL File]
193537-14-3.mol |
| Hazard Information | Back Directory | [Synthesis]
General Steps:
Step a. Synthesis of 2-amino-4,7-dihydro-5H-thieno[2,3-c]pyridine-3,6-dicarboxylic acid 6-tert-butyl 3-ethyl ester
In anhydrous ethanol (50 mL), N-tert-butoxycarbonyl-4-piperidone (12.9 g), ethyl cyanoacetate (7.345 g), and sulfur powder (2.080 g) were mixed, followed by the addition of triethylamine (9 mL). The reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, the precipitate was collected by filtration and washed with ethanol to afford 2-amino-4,5-dihydrothieno[2,3-c]pyridine-3,6(7H)-dicarboxylic acid-6-tert-butyl ester (18.7 g, 88% yield).
Product characterization data:
1H NMR (300 MHz, CDCl3): δ 6.02 (s, 2H), 4.31 (s, 2H), 4.23 (q, 2H, J = 7.2 Hz), 3.58 (t, 2H, J = 6.0 Hz), 2.72-2.80 (br s, 2H), 1.44 (s, 9H), 1.30 (t, 3H, J = 7.2 Hz).
LC-MS (ESI) m/z: 327.0 (M + H)+. | [References]
[1] Synlett, 2010, # 9, p. 1351 - 1354
[2] Patent: US2010/120805, 2010, A1. Location in patent: Page/Page column 44
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 20, p. 7316 - 7326
[4] Patent: WO2009/33581, 2009, A1. Location in patent: Page/Page column 62
[5] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3101 - 3112 |
|
|