Cesium carbonate → HCID 118390048, compound

HRID 1478065Notes

Reaction equation

HRID 1478065 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:26][CH2:25][C:12]3([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[CH2:11][CH2:10]2)[C:5]([Cl:27])=[CH:4][N:3]=1.Cl.[CH:29]1([C:32]2[NH:36][N:35]=[C:34]([NH2:37])[CH:33]=2)[CH2:31][CH2:30]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.C(O[Pd]OC(=O)C)(=O)C>[Cl:27][C:5]1[C:6]([NH:8][CH:9]2[CH2:10][CH2:11][C:12]3([CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:16][CH2:17]3)[CH2:25][CH2:26]2)=[N:7][C:2]([NH:37][C:34]2[CH:33]=[C:32]([CH:29]3[CH2:31][CH2:30]3)[NH:36][N:35]=2)=[N:3][CH:4]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 164953395-Cyclopropyl-1H-pyrazol-3-amine--hydrogen chloride (1/1)HCID 118390013Tert-butyl 3-[(2,5-dichloropyrimidin-4-yl)amino]-9-azaspiro[5.5]undecane-9-carboxylate

Product 1

HCID 118390048HCID 118390048, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 9-((2,5-dichloropyrimidin-4-yl)amino)-3-azaspiro[5.5]undecane-3-carboxylate (506 mg, 1.22 mmol), 5-cyclopropyl-1H-pyrazol-3-amine hydrochloride (272 mg, 1.70 mmol), cesium carbonate (1.176 g, 3.609 mmol), [1-(2-diphenylphosphanyl-1-naphthyl)-2-naphthyl]-diphenyl-phosphane (147.6 mg, 0.2370 mmol) and diacetoxypalladium (53.8 mg, 0.240 mmol) in anhydrous dioxane (10 mL) stirred in a sealed tube under the microwave radiation at 150° C. for 2 h. Then the reaction mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=30/1) to give the title compound as a light yellow solid (364 mg, 59.5%).

Workup

  1. concentrationThen the reaction mixture was concentrated in vacuo
  2. customthe residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=30/1)

Sources & evidence

ORD record
ord-4f290108bc6044ea83366bb703a23428
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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