Ethyl orthoformate → HCID 67210950, compound

HRID 452165Notes

Reaction equation

[CH3:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][CH2:12][CH3:13])[N:7]([CH2:14][C:15]3[CH:34]=[CH:33][C:18]4/[C:19](=[CH:28]\[C:29]([NH:31][NH2:32])=[O:30])/[C:20]5[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=5[O:22][CH2:23][C:17]=4[CH:16]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:35](OC(OCC)OCC)C>>[CH3:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][CH2:12][CH3:13])[N:7]([CH2:14][C:15]3[CH:34]=[CH:33][C:18]4/[C:19](=[CH:28]\[C:29]5[O:30][CH:35]=[N:32][N:31]=5)/[C:20]5[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=5[O:22][CH2:23][C:17]=4[CH:16]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 31214Ethyl orthoformate

HCID 67210421HCID 67210421, compound

Product 1

HCID 67210950HCID 67210950, compoundYield 16%

Conditions

Temperature: 120 °C

Procedure

To (E)-2-[8-(4-methyl-2-propylbenzimidazol-1-yl)methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene]acetohydrazide (118 mg, 0.25 mmol) obtained in Example 106, step 1 was added triethoxymethane (2.1 mL), and the mixture was stirred at 120° C. for 5 hr. The mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30 to 10/90) to give the title compound (compound 107) (18 mg, 16%).

Workup

concentrationThe mixture was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30 to 10/90)

Sources & evidence

ORD record: ord-666e53c80b2143af8c2707c9ee5708d4
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486980B2

Reaction notes

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