Cesium carbonate → HCID 86648240, compound

HRID 1922892Notes

Reaction equation

HRID 1922892 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]2[N:19]=[C:18]3[C:14]([N:15]=[C:16]([CH2:21][N:22]4[CH2:27][CH2:26][CH:25]([C:28]([OH:31])([CH3:30])[CH3:29])[CH2:24][CH2:23]4)[N:17]3[CH3:20])=[C:13]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[N:12]=2)[N:3]=1.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(=O)([O-])[O-].[Cs+].[Cs+].[C:86](=[NH:99])([C:93]1[CH:98]=[CH:97][CH:96]=[CH:95][CH:94]=1)[C:87]1[CH:92]=[CH:91][CH:90]=[CH:89][CH:88]=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:87]1([C:86](=[N:99][C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]([C:11]3[N:19]=[C:18]4[C:14]([N:15]=[C:16]([CH2:21][N:22]5[CH2:27][CH2:26][CH:25]([C:28]([OH:31])([CH3:30])[CH3:29])[CH2:24][CH2:23]5)[N:17]4[CH3:20])=[C:13]([N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)[N:12]=3)[N:3]=2)[C:93]2[CH:94]=[CH:95][CH:96]=[CH:97][CH:98]=2)[CH:92]=[CH:91][CH:90]=[CH:89][CH:88]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 67492680HCID 67492680, compound

Product 1

HCID 86648240HCID 86648240, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-(1-((2-(3-iodo-1H-indazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-ol (0.1 g), tris(dibenzylideneacetone)dipalladium(0) (3 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (5.6 mg) and cesium carbonate (74 mg) in 1,4-dioxane (0.5 mL) was added benzophenone imine (40 μL). The reaction was heated at 120° C. until complete, about 90 minutes. The crude reaction mixture was loaded onto silica and purified by flash column chromatography to afford 2-(1-((2-(3-(diphenylmethyleneamino)-1H-indazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-ol.

Workup

  1. customThe crude reaction mixture
  2. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-e82f7023963c426f8a7f162858d46a39
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

Loading…