Cesium carbonate → methyl 4-[3-[(E)-(4-tert-butylphenyl)methylideneamino]oxypropoxy]-2-[[(E)-3-(4-phenylphenyl)prop-2-enoyl]amino]benzoate

HRID 29693Notes

Reaction equation

HRID 29693 reaction equation
[CH3:1][O:2][C:3](=[O:32])[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:31])/[CH:17]=[CH:18]/[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:39]([C:43]1[CH:51]=[CH:50][C:46]([CH:47]=[N:48][OH:49])=[CH:45][CH:44]=1)([CH3:42])([CH3:41])[CH3:40]>CC(C)=O>[C:22]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:21]=[CH:20][C:19](/[CH:18]=[CH:17]/[C:16]([NH:15][C:5]2[CH:6]=[C:7]([O:10][CH2:11][CH2:12][CH2:13][O:49]/[N:48]=[CH:47]/[C:46]3[CH:45]=[CH:44][C:43]([C:39]([CH3:42])([CH3:40])[CH3:41])=[CH:51][CH:50]=3)[CH:8]=[CH:9][C:4]=2[C:3]([OH:32])=[O:2])=[O:31])=[CH:24][CH:23]=1.[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][O:49]/[N:48]=[CH:47]/[C:46]2[CH:50]=[CH:51][C:43]([C:39]([CH3:42])([CH3:41])[CH3:40])=[CH:44][CH:45]=2)=[CH:6][C:5]=1[NH:15][C:16](=[O:31])/[CH:17]=[CH:18]/[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 1275951N-[(4-tert-butylphenyl)methylidene]hydroxylamineHCID 69205359HCID 69205359, compound

Product 2

HCID 112845964-[3-[(E)-(4-tert-butylphenyl)methylideneamino]oxypropoxy]-2-[[(E)-3-(4-phenylphenyl)prop-2-enoyl]amino]benzoic acidHCID 87734082methyl 4-[3-[(E)-(4-tert-butylphenyl)methylideneamino]oxypropoxy]-2-[[(E)-3-(4-phenylphenyl)prop-2-enoyl]amino]benzoateYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The desired product was prepared using a procedure similar to Step 6 of example 34. Thus, 2-{[(2E)-3-(1,1′-biphenyl-4-yl)prop-2-enoyl]amino}-4-(3-bromopropoxy)benzoic acid methyl ester (0.299 g, 0.605 mmol) was reacted with cesium carbonate (0.414 g, 1.271 mmol) and 4-tert-butyl-benzaldehyde oxime (0.118 g, 0.665 mmol) in acetone (30 ml) to give 2-{[(2E)-3-(1,1′-biphenyl-4-yl)prop-2-enoyl]amino}-4-[3-({[(1E)-(4-tert-butylphenyl)methylidene]amino}oxy)propoxy]benzoic acid methyl ester (0.148 g, 0.251 mmol, 41%) as a pale yellow solid, mp 120-122° C. 1H NMR (DMSO-d6) δ 1.25 (s, 9H), 2.10-2.22 (m, 2H), 3.85 (s, 3H), 4.18 (t, 2H), 4.26 (t, 2H), 6.80 (dd, 1H), 6.95 (d, 1H), 7.37-7.54 (m, 7H), 7.62-7.78 (m, 5H), 7.83 (d, 2H), 7.97 (d, 1H), 8.22 (s, 1H), 8.30 (dd, 1H), 11.16 (s, 1H); mass spectrum [ES(−)], m/z 589 (M−H)−.

Sources & evidence

ORD record
ord-788b1b68526f4f49b88672d9ba3b76bc
Source dataset
uspto-grants-2008_09
Patent number
US07420083B2

Reaction notes

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