16-Amino-5-bromo-4-(phenylmethoxy)-2-oxa-10-azatricyclo[12.2.2.13,7]nonadeca-3,5,7(19),14,16,17-hexaen-11-one

Base Information

Chemical Name:16-Amino-5-bromo-4-(phenylmethoxy)-2-oxa-10-azatricyclo[12.2.2.13,7]nonadeca-3,5,7(19),14,16,17-hexaen-11-one
CAS No.:907602-46-4
Molecular Formula:C₂₄H₂₃BrN₂O₃
Molecular Weight:467.362
Hs Code.:
DSSTox Substance ID:DTXSID001108974

Synonyms:DTXSID001108974;16-Amino-5-bromo-4-(phenylmethoxy)-2-oxa-10-azatricyclo[12.2.2.13,7]nonadeca-3,5,7(19),14,16,17-hexaen-11-one;907602-46-4

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Chemical Property of 16-Amino-5-bromo-4-(phenylmethoxy)-2-oxa-10-azatricyclo[12.2.2.13,7]nonadeca-3,5,7(19),14,16,17-hexaen-11-one

Chemical Property:

XLogP3:4.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:466.08921
Heavy Atom Count:30
Complexity:557

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:C1CC(=O)NCCC2=CC(=C(C(=C2)Br)OCC3=CC=CC=C3)OC4=C(C=C1C=C4)N

Technology Process of 16-Amino-5-bromo-4-(phenylmethoxy)-2-oxa-10-azatricyclo[12.2.2.13,7]nonadeca-3,5,7(19),14,16,17-hexaen-11-one

There total 7 articles about 16-Amino-5-bromo-4-(phenylmethoxy)-2-oxa-10-azatricyclo[12.2.2.13,7]nonadeca-3,5,7(19),14,16,17-hexaen-11-one 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: 73.0%

: 907602-45-3
4-benzyloxy-5-bromo-16-nitro-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]-nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,4,6,14⁽¹⁸⁾,15-hexaen-11-one

: 907602-46-4
16-amino-4-benzyloxy-5-bromo-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]-nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,4,6,14⁽¹⁸⁾,15-hexaen-11-one

Guidance literature:: With chromium dichloride; In N,N-dimethyl-formamide; at 20 ℃; for 12h;
DOI:10.1021/jm050708u

Reference yield:

: 907602-44-2
3-(4-fluoro-3-nitrophenyl)propionic acid methyl ester

: 907602-46-4
16-amino-4-benzyloxy-5-bromo-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]-nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,4,6,14⁽¹⁸⁾,15-hexaen-11-one

Guidance literature:: Multi-step reaction with 4 steps

1: 86 percent / LiOH / tetrahydrofuran; methanol; H₂O

2: 72 percent / HOBt; EDCI / CH₂Cl₂ / 1 h / 20 °C

3: 85 percent / K₂CO₃; 4 Angstroem sieves / dimethylsulfoxide / 3 h / 20 °C

4: 73 percent / CrCl₂ / dimethylformamide / 12 h / 20 °C

With chromium dichloride; lithium hydroxide; 4 A molecular sieve; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jm050708u

Reference yield:

: 907602-39-5
5-(2-aminoethyl)-2-benzyloxy-3-bromophenol

: 907602-46-4
16-amino-4-benzyloxy-5-bromo-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]-nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,4,6,14⁽¹⁸⁾,15-hexaen-11-one

Guidance literature:: Multi-step reaction with 3 steps

1: 72 percent / HOBt; EDCI / CH₂Cl₂ / 1 h / 20 °C

2: 85 percent / K₂CO₃; 4 Angstroem sieves / dimethylsulfoxide / 3 h / 20 °C

3: 73 percent / CrCl₂ / dimethylformamide / 12 h / 20 °C

With chromium dichloride; 4 A molecular sieve; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jm050708u