Phenol → HCID 58525342, compound

HRID 1626358Notes

Reaction equation

HRID 1626358 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:28]=[CH:27][C:16]([C:17]([NH:19][CH:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)=[O:18])=[CH:15][C:14]=2[O:29][CH3:30])[N:3]=1.[C:31]1([OH:37])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.N1C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CO>[CH3:30][O:29][C:14]1[CH:15]=[C:16]([CH:27]=[CH:28][C:13]=1[NH:12][C:4]1[N:3]=[C:2]([O:37][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=1)[C:17]([NH:19][CH:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1)=[O:18]

Participants

7

Reactant 4

HCID 996PhenolHCID 1049PyridineHCID 10796Cesium carbonateHCID 582009164-(4-chloro-5-trifluoromethyl-pyrimidin-2-ylamino)-3-methoxy-N-(1-methyl-piperidin-4-yl)-benzamide

Product 1

HCID 58525342HCID 58525342, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

4-(4-chloro-5-trifluoromethyl-pyrimidin-2-ylamino)-3-methoxy-N-(1-methyl-piperidin-4-yl)-benzamide (50 mg) and phenol (21.3 mg) are dissolved in dioxane (0.3 mL). Pyridine (36.4 μL) and Cs2CO3 (235 mg) are added and the suspension is stirred overnight at 80° C. Then the reaction mixture is diluted with methanol (5 mL) and mixed with isolute. The solvent is eliminated in vacuo and then the mixture is purified by preparative HPLC. (PTK2 IC50=35 nmol)

Workup

  1. additionmixed with isolute
  2. customthe mixture is purified by preparative HPLC

Sources & evidence

ORD record
ord-bbc8a45a5ada46bdb8e6b87c892f7dd5
Source dataset
uspto-grants-2014_07
Patent number
US08785464B2

Reaction notes

Loading…