Cesium carbonate → HCID 57815323, compound

HRID 385690Notes

Reaction equation

HRID 385690 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:39])[N:9]2[CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([N:20]([CH2:28][C:29]3[N:34]=[CH:33][C:32]4[O:35][CH2:36][CH2:37][O:38][C:31]=4[CH:30]=3)[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:16][CH2:15]2)=[N:4][CH:3]=1.[C:40](=[O:47])([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])[NH2:41].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>[C:43]([O:42][C:40]([NH:41][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:39])[N:9]2[CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([N:20]([CH2:28][C:29]3[N:34]=[CH:33][C:32]4[O:35][CH2:36][CH2:37][O:38][C:31]=4[CH:30]=3)[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:16][CH2:15]2)=[N:4][CH:3]=1)=[O:47])([CH3:46])([CH3:45])[CH3:44]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 77922tert-Butyl carbamateHCID 57815264HCID 57815264, compound

Product 1

HCID 57815323HCID 57815323, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 0.85 g of tert-butyl (1-(2-(7-bromo-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)(2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)carbamate in 5 mL of 1,4-dioxane, 0.20 g of tert-butyl carbamate, 0.69 g of cesium carbonate and 13 mg of tris(benzylideneacetone)dipalladium and 24 mg of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene were added, and the mixture was stirred at 90° C. for 38 hours under a nitrogen atmosphere. After cooling to room temperature, the insoluble substance was separated by filtration, and the filtrated solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography using silica gel; Silica Gel 60 made by KANTO CHEMICAL CO., INC., and an eluent of hexane:ethyl acetate=33:67 to 5:95 to obtain 0.68 g of tert-butyl (1-(2-(7-((tert-butoxycarbonyl)amino)-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)(2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)carbamate as a white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe insoluble substance was separated by filtration
  3. concentrationthe filtrated solution was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6372c4566cbc4f12ab1c63fb7148acff
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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