Cesium carbonate → HCID 57815425, compound

HRID 385646Notes

Reaction equation

HRID 385646 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:10]=[CH:9][C:8](=[O:11])[N:7]([CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][CH:17]([N:20]([CH2:28][C:29]4[N:34]=[CH:33][C:32]5[O:35][CH2:36][CH2:37][O:38][C:31]=5[CH:30]=4)[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:16][CH2:15]3)[C:6]=2[N:39]=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:3]=[CH:4][C:5]2[N:10]=[CH:9][C:8](=[O:11])[N:7]([CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][CH:17]([N:20]([CH2:28][C:29]4[N:34]=[CH:33][C:32]5[O:35][CH2:36][CH2:37][O:38][C:31]=5[CH:30]=4)[C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:26])[CH3:24])[CH2:18][CH2:19]3)[C:6]=2[N:39]=1)=[O:47])([CH3:46])([CH3:45])[CH3:44]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 77922tert-Butyl carbamateHCID 57815368HCID 57815368, compound

Product 1

HCID 57815425HCID 57815425, compoundYield 61.9%

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
85 °C

Procedure

To a solution of 0.11 g of tert-butyl (1-(2-(6-chloro-3-oxopyrido(2,3-b)pyrazin-4(3H)-yl)ethyl)piperidin-4-yl)(2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)carbamate in 3 mL of dioxane, 25 mg of tert-butyl carbamate and 82 mg of cesium carbonate were added. Thereto were added 2.5 mg of tris(dibenzylideneacetate)dipalladium(0) and 3.1 mg of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene under an argon atmosphere. The mixture was stirred at 80 to 90° C. for 2 hours under an argon atmosphere. The insoluble substance was filtered off, and the solvent was distilled off under reduced pressure. The resultant residue was purified by basic silica gel column chromatography using an eluent of chloroform:methanol=20:1 to obtain 78 mg of tert-butyl (1-(2-(6-((tert-butoxycarbonyl)amino)-3-oxopyrido(2,3-b)pyrazin-4(3H)-yl)ethyl)piperidin-4-yl)(2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)carbamate as a light brown oily substance.

Workup

  1. filtrationThe insoluble substance was filtered off
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe resultant residue was purified by basic silica gel column chromatography

Sources & evidence

ORD record
ord-f1b3d4889a124fd88a190c4d5772dc92
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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