HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → Methyl 13-cyclohexyl-6-(2,5,13,13-tetramethyl-9,9-dioxido-11-oxo-12-oxa-9-thia-2,5,10-triazatetradec-1-yl)-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | Tert-butyl[(3-{methyl[2-(methylamino)ethyl]amino}propyl)sulfonyl]carbamate | HCID 86640308 | — |
| Reactant | Methyl 13-cyclohexyl-6-formyl-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate | HCID 86640311 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | Methyl 13-cyclohexyl-6-(2,5,13,13-tetramethyl-9,9-dioxido-11-oxo-12-oxa-9-thia-2,5,10-triazatetradec-1-yl)-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate | HCID 66674850 | — |
Reaction Steps
Methyl 13-cyclohexyl-6-formyl-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate was dissolved in MeOH (0.04 M), HOAc (5 eq.) and tert-butyl[(3-{methyl[2-(methylamino)ethyl]amino}propyl)sulfonyl]carbamate (2 eq. Example 15, steps 1-3) were added followed by Et3N (3 eq.) and the mixture was stirred for 5 min. NaCNBH3 (2 eq.) was added and the mixture was stirred for 18 h. All volatiles were evaporated and the residual material was dissolved in EtOAc. The solution was extracted with sat. aq. NaHCO3, water and brine. After drying over Na2SO4 all volatiles were evaporated in vacuo and the compound was used without purification in the next reaction. (ES) m/z 697 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08101595B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-8784ee27327b466594d63f005d989929 |
| Source note | uspto-grants-2012_01 |