Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 421967Generated: October 31, 2026

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

https://huagongshe.com/reaction/421967

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantTriethylamineHCID 8471—
ReactantSodium cyanoborohydrideHCID 5003444—
ReactantTert-butyl[(3-{methyl[2-(methylamino)ethyl]amino}propyl)sulfonyl]carbamateHCID 86640308—
ReactantMethyl 13-cyclohexyl-6-formyl-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylateHCID 86640311—
SolventMethanolHCID 887—
ProductMethyl 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-carboxylateHCID 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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08101595B2
Source datasetuspto-grants-2012_01
ORD IDord-8784ee27327b466594d63f005d989929
Source noteuspto-grants-2012_01