Cesium carbonate → methyl 2-[[4-(trifluoromethoxy)benzoyl]amino]-4-[3-[(E)-[4-(trifluoromethyl)phenyl]methylideneamino]oxypropoxy]benzoate

HRID 29679Notes

Reaction equation

HRID 29679 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13]Br)=[CH:6][C:5]=1[NH:15][C:16](=[O:28])[C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1.[F:30][C:31]([F:42])([F:41])[C:32]1[CH:40]=[CH:39][C:35]([CH:36]=[N:37][OH:38])=[CH:34][CH:33]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][O:38]/[N:37]=[CH:36]/[C:35]2[CH:34]=[CH:33][C:32]([C:31]([F:30])([F:42])[F:41])=[CH:40][CH:39]=2)=[CH:6][C:5]=1[NH:15][C:16](=[O:28])[C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 3056297Benzaldehyde, 4-(trifluoromethyl)-, oximeHCID 692101914-(3-Bromo-propoxy)-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester

Product 1

HCID 87734096methyl 2-[[4-(trifluoromethoxy)benzoyl]amino]-4-[3-[(E)-[4-(trifluoromethyl)phenyl]methylideneamino]oxypropoxy]benzoateYield 78%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

This compound was produced using similar methods as those used in Step 5, example 27, starting with 4-(3-bromo-propoxy)-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester (0.46 g, 0.97 mmol), 4-trifluoromethyl-benzaldehyde oxime (0.19 g, 1.01 mmol) and cesium carbonate (1.26 g, 3.86 mmol) in acetone (35 mL). The crude material was purified by flash chromatography through silica gel using diethyl ether/hexanes (0/100 gradient to 10/90) to give 2-{[4-(trifluoromethoxy)benzoyl]amino}-4-{3-[({(1E)-[4-(trifluoromethyl)phenyl]methylidene}amino)oxy]propoxy}benzoic acid methyl ester (0.44 g, 78%) as a white solid. 1H NMR (500 MHz, DMSO-d6); δ 11.92 (s, 1H), 8.38 (s, 1H), 8.32 (d, 1H), 8.05 (d, 2H), 7.97 (d, 1H), 7.80-7.21 (AA′BB′, 4H), 7.60 (d, 2H), 6.82 (dd, 1H), 4.34 (t, 2H), 4.21 (t, 2H), 3.87 (s, 3H), 2.18 (m, 2H).

Workup

  1. customThis compound was produced
  2. customThe crude material was purified by flash chromatography through silica gel

Sources & evidence

ORD record
ord-89411de4f979419fba40866ce6961996
Source dataset
uspto-grants-2008_09
Patent number
US07420083B2

Reaction notes

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