1,2-Dichloroethane → N-(3-Methyl-4-isoxazolyl)-5-(1-methyl-1H-pyrazol-4-yl)-4-(4-morpholinylcarbonyl)-2-[(phenylmethyl)oxy]benzamide

HRID 2204749Notes

Reaction equation

HRID 2204749 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:8]([C:24]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[O:25])=[CH:9][C:10]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:11]([CH:15]=2)[C:12](O)=[O:13])[CH:4]=[N:3]1.C(N(C(C)C)CC)(C)C.[CH3:41][C:42]1[C:46]([NH2:47])=[CH:45][O:44][N:43]=1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CN(C)C=O>[CH3:41][C:42]1[C:46]([NH:47][C:12](=[O:13])[C:11]2[CH:15]=[C:7]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)[C:8]([C:24]([N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)=[O:25])=[CH:9][C:10]=2[O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:45][O:44][N:43]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 138042843-Methyl-1,2-oxazol-4-amineHCID 666111175-(1-Methyl-1H-pyrazol-4-yl)-4-(4-morpholinylcarbonyl)-2-[(phenylmethyl)oxy]benzoic acid

Product 1

HCID 66635116N-(3-Methyl-4-isoxazolyl)-5-(1-methyl-1H-pyrazol-4-yl)-4-(4-morpholinylcarbonyl)-2-[(phenylmethyl)oxy]benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(1-methyl-1H-pyrazol-4-yl)-4-(4-morpholinylcarbonyl)-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 26; 44 mg, 0.10 mmol) in N,N-dimethylformamide (5 ml) was added diisopropylethylamine (0.04 ml, 0.21 mmol), 3-methyl-4-isoxazolamine (20.48 mg, 0.21 mmol), 1-hydroxy-7-azabenzotriazole (21.32 mg, 0.16 mmol) and EDC (34.0 mg, 0.18 mmol). The reaction was stirred for 18 hours and then the solvent was removed in vacuo. The residue was purified by MDAP to yield the title compound as a white solid. 43 mg.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by MDAP

Sources & evidence

ORD record
ord-2d9ddaacb5a641f5b14d2b8caf25465c
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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