1,2-Dichloroethane → N-(3-Methyl-4-isoxazolyl)-2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzamide

HRID 1623802Notes

Reaction equation

HRID 1623802 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[CH:14][C:10]=2[C:11]([OH:13])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)CCl.C1C=[CH:30][C:31]2[N:36]([OH:37])N=[N:34][C:32]=2[CH:33]=1.CC1C(N)=CON=1>CN(C)C=O.O>[CH3:30][C:31]1[C:32]([NH:34][C:11](=[O:13])[C:10]2[CH:14]=[C:15]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[CH:16]=[CH:17][C:9]=2[O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:33][O:37][N:36]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 138042843-Methyl-1,2-oxazol-4-amineHCID 66990482HCID 66990482, compound

Product 1

HCID 67106998N-(3-Methyl-4-isoxazolyl)-2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzoic acid (may be prepared as described in Description 79; 0.12 g, 0.36 mmol), EDC (0.14 g, 0.72 mmol) and HOBT (0.11 g, 0.72 mmol) in N,N-dimethylformamide (2 ml) was stirred in air at room temperature for 1 h, then 3-methyl-4-isoxazolamine (may be prepared as described in Description 91; 100 mg, 1.02 mmol) was added in one charge. The reaction mixture was stirred at 25° C. overnight. The reaction mixture was diluted with water (25 ml). The solid was filtered, washed with water (30 ml) and methanol (5 ml×2), and dried in vacuo to yield the title compound as a grey solid. 72 mg.

Workup

  1. additioncharge
  2. stirringThe reaction mixture was stirred at 25° C. overnight
  3. filtrationThe solid was filtered
  4. washwashed with water (30 ml) and methanol (5 ml×2)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-55e95e59ddf14a76835c54ae000800d0
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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