Tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1h)-carboxylate

Base Information

• Chemical Name: Tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1h)-carboxylate
• CAS No.: 164148-92-9
• Molecular Formula: C14H20N2O2
• Molecular Weight: 248.325
• Hs Code.: 2933499090
• European Community (EC) Number: 672-211-1
• DSSTox Substance ID: DTXSID20373344
• Wikidata: Q72438334
• Mol file: 164148-92-9.mol

Synonyms:164148-92-9;6-amino-2-n-boc-1,2,3,4-tetrahydro-isoquinoline;tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1h)-carboxylate;6-Amino-2-N-BOC-1,2,3,4-tetrahydroisoquinoline;tert-butyl 6-amino-3,4-dihydro-1H-isoquinoline-2-carboxylate;2-Boc-6-Amino-1,2,3,4-tetrahydroisoquinoline;6-Amino-2-Boc-1,2,3,4-tetrahydroisoquinoline;tert-butyl 6-amino-1,2,3,4-tetrahydroisoquinoline-2-carboxylate;6-amino-3,4-dihydro-1h-isoquinoline-2-carboxylic acid tert-butyl ester;MFCD03426351;SCHEMBL61143;DTXSID20373344;OLOIFCYZWOTWRO-UHFFFAOYSA-N;BCP26934;CS-M0025;AKOS015854639;PB15747;AC-23291;DS-11163;SY056871;A3644;AM20030104;FT-0643583;EN300-396901;6-amino-2N-Boc-1,2,3,4-tetrahydroisoquinoline;Q-102314;Z1741960800;6-Amino-2-(t-butyloxycarbonyl)-1,2,3,4-tetrahydroisoquinoline;6-amino-2-N-Boc-1,2,3,4-tetrahydro-isoquinoline, AldrichCPR;tert-butyl 6-amino-3,4-dihydro-2(1H)-isoquinolinecarboxylate;tert-butyl 6-amino-3,4dihydroisoquinoline-2(1h)-carboxylate;tert-butyl6-amino-3,4-dihydroisoquinoline-2(1h)-carboxylate;1,1-Dimethylethyl 6-amino-3,4-dihydro-2(1H)-isoquinolinecarboxylate;6-amino-3,4-dihydro-1H-isoquinoline-2-caboxyiic acid tert-butyl ester;6-amino-3,4-dihydro-1h-isoquinoline2-carboxylic acid tert-butyl ester;6-Amino-3,4dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester;6Amino-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester;2(1H)-ISOQUINOLINECARBOXYLIC ACID, 6-AMINO-3,4-DIHYDRO-, 1,1-DIMETHYLETHYL ESTER

Chemical Property of Tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1h)-carboxylate

Chemical Property:

• Vapor Pressure: 1.94E-06mmHg at 25°C
• Refractive Index: 1.569
• Boiling Point: 394.7 °C at 760 mmHg
• PKA: 4.35±0.20(Predicted)
• Flash Point: 192.5 °C
• PSA: 55.56000
• Density: 1.145 g/cm³
• LogP: 3.08110
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 248.152477885
• Heavy Atom Count: 18
• Complexity: 311

Purity/Quality:

98%,99%, ^*data from raw suppliers

6-Amino-2-N-Boc-1,2,3,4-tetrahydroisoquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:
• Hazard Codes: Xn,N
• Statements: 36/37/38-50-22
• Safety Statements: 26-36/37/39-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC2=C(C1)C=CC(=C2)N
• Uses: 6-Amino-2-N-Boc-1,2,3,4-tetrahydroisoquinoline is used as a reagent in the preparation of potent and long acting oral factor Xa inhibitors.

Technology Process of Tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1h)-carboxylate

There total 13 articles about Tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1h)-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

6-Nitro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (186390-79-4) → tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate (164148-92-9)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; at 20 ℃;

DOI:10.1021/acs.jmedchem.0c01488

Reference yield: 91.0%

tert-butyl 6-benzyloxycarbonylamino-3,4-dihydro-1H-isoquinoline-2-carboxylate (1154424-63-1) → tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate (164148-92-9)

Guidance literature:

With ammonium formate; palladium(II) hydroxide; In ethanol; for 6h; Reflux;

Reference yield: 91.0%

di-tert-butyl dicarbonate (24424-99-5) + 1,2,3,4-tetrahydroisoquinolin-6-amine (72299-67-3) → tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate (164148-92-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide; at 40 ℃; under 7500.75 Torr; Flow reactor;

DOI:10.1002/ejoc.201801684

upstream raw materials:

6-Nitro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

di-tert-butyl dicarbonate

1,2,3,4-tetrahydroisoquinolin-6-amine

tert-butyl 6-benzyloxycarbonylamino-3,4-dihydro-1H-isoquinoline-2-carboxylate

Downstream raw materials:

tert-butyl 6-[(2-isopropoxy-4-methylbenzoyl)amino]-3,4-dihydro-2(1H)-isoquinolinecarboxylate

6-(Toluene-4-sulfonylamino)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert butyl ester

6-[(4'-Trifluoromethyl-biphenyl-2-carbonyl)-amino]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

1,1-dimethylethyl 6-[({1-[(3,4-dichlorophenyl)methyl]-1H-pyrazol-4-yl}carbonyl)amino]-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Refernces

• 1、 Luise, Nicola,Wyatt, Eleanor W.,Tarver, Gary J.,Wyatt, Paul G.. "A Continuous Flow Strategy for the Facile Synthesis and Elaboration of Semi-Saturated Heterobicyclic Fragments". . p. 1341 - 1349. Retrieved 2019/01/14.
• 2、 -. "COMPOUNDS AS HEPATITIS C VIRUS (HCV) INHIBITORS AND USES THEREOF IN MEDICINE". Paragraph 00131. . Retrieved 2016/01/25.