4-Methylmorpholine → HCID 67545460, compound

HRID 2059712Notes

Reaction equation

HRID 2059712 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[N:14]2[CH:15]=[CH:16][CH:17]=[N:18][C:13]2=[N:12][C:11]=1[C:19]1[C:27]([O:28][CH3:29])=[CH:26][C:25]([O:30][CH3:31])=[CH:24][C:20]=1[C:21]([OH:23])=O.Cl.CON.C[N:37]1CCO[CH2:39][CH2:38]1>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[N:14]2[CH:15]=[CH:16][CH:17]=[N:18][C:13]2=[N:12][C:11]=1[C:19]1[C:27]([O:28][CH3:29])=[CH:26][C:25]([O:30][CH3:31])=[CH:24][C:20]=1[C:21]([NH:37][CH2:38][CH3:39])=[O:23]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 59509174HCID 59509174, compound

Product 1

HCID 67545460HCID 67545460, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

400 mg of 2-[3-(2,6-dichlorophenylamino)imidazo[1,2-a]pyrimidin-2-yl]-3,5-dimethoxybenzoic acid, 73 mg of O-methylhydroxylamine hydrochloride, 200 mg of DAPECI and 88 mg of 4-methylmorpholine are dissolved in 1 ml of DMF and stirred at RT for 1 hour. The solvent is removed, and the residue is purified by column chromatography (heptane/ethyl acetate), giving 90 mg (21%) of 2-[3-(2,6-dichlorophenylamino)imidazo[1,2-a]pyrimidin-2-yl]-N-ethyl-3,5-dimethoxybenzamide (A17) as solid; MS-FAB (M+H+) 489.7; Rf (polar method): 1.61 min.

Workup

  1. customThe solvent is removed
  2. customthe residue is purified by column chromatography (heptane/ethyl acetate)

Sources & evidence

ORD record
ord-24c8c4d0a4d14b998e7808a941d5dde2
Source dataset
uspto-grants-2012_10
Patent number
US08278312B2

Reaction notes

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