HuagongsheHuagongshe Chemistry Print Report · For research reference only
(R)-3-(2-(2-(tert-Butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino)-2-methylpropyl)benzaldehyde → (R)-5-(1-(tert-Butyldimethylsilyloxy)-2-(1-(3-((4-(5-isopropylthiophene-3-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)-2-methylpropan-2-ylamino)ethyl)-8-hydroxyquinolin-2(1H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (R)-3-(2-(2-(tert-Butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino)-2-methylpropyl)benzaldehyde | HCID 57989117 | — |
| Reactant | (5-Isopropylthiophen-3-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone | HCID 57989215 | — |
| Product | (R)-5-(1-(tert-Butyldimethylsilyloxy)-2-(1-(3-((4-(5-isopropylthiophene-3-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)-2-methylpropan-2-ylamino)ethyl)-8-hydroxyquinolin-2(1H)-one | HCID 57989329 | — |
Reaction Steps
The subtitled compound was prepared using a similar method to that described in Example 14, step b) using (R)-3-(2-(2-(tert-butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino)-2-methylpropyl)benzaldehyde (0.32 g) (Example 275, step h) and (5-isopropylthiophen-3-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone (0.21 g) (Example 275, step i)). The crude product was purified by flash silica chromatography, 8% methanol in dichloromethane with 1% 880 aqueous ammonia. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.31 g.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08629271B2 |
| Source dataset | uspto-grants-2014_01 |
| ORD ID | ord-6379a9ad7b5441dd86c801ddc7dd9cd0 |
| Source note | uspto-grants-2014_01 |