Acetamide → HCID 90418656, compound

HRID 709999Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([C:16]3[C:17]([O:26][CH3:27])=[N:18][C:19]([NH:22][CH:23]([CH3:25])[CH3:24])=[N:20][CH:21]=3)=[N:13][C:14]=2[CH3:15])[CH:5]=[CH:4][N:3]=1.[C:28]([NH2:31])(=[O:30])[CH3:29].C([O-])([O-])=O.[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>O1CCOCC1.CCOC(C)=O.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]>[CH:23]([NH:22][C:19]1[N:18]=[C:17]([O:26][CH3:27])[C:16]([C:12]2[N:13]=[C:14]([CH3:15])[C:9]([O:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:31][C:28](=[O:30])[CH3:29])[CH:7]=3)=[CH:10][CH:11]=2)=[CH:21][N:20]=1)([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of Example C4 in dioxane (3 mL) was treated with acetamide (0.06 g, 1.0 mmol), Cs2CO3 (0.11 g, 0.34 mmol), X-Phos (0.03 g, 0.077 mmol) and Pd2(dba)3 (0.03 g, 0.034 mmol) and heated at 80° C. overnight. The mixture was diluted with EtOAc, the solids removed via filtration through diatomaceous earth, washed with EtOAc and the filtrate was washed with water, then brine, dried over Na2SO4, concentrated to dryness and purified by silica gel chromatography (MeOH/DCM) to afford N-(4-((6-(2-(isopropylamino)-4-methoxypyrimidin-5-yl)-2-methylpyridin-3-yl)oxy)pyridin-2-yl)acetamide (60 mg, 36%).

Workup

customthe solids removed via filtration through diatomaceous earth
washwashed with EtOAc
washthe filtrate was washed with water
dry with materialbrine, dried over Na2SO4
concentrationconcentrated to dryness
custompurified by silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record: ord-ee60c93b04084394bf862a92c390b444
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181223B2

Reaction notes

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