Ethyl orthoformate → HCID 67210908, compound

HRID 452134Notes

Reaction equation

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

Participants

Reactant 2

HCID 31214Ethyl orthoformate

HCID 178506457HCID 178506457, compound

Product 1

HCID 67210908HCID 67210908, compoundYield 42%

Conditions

Temperature: 80 °C

Procedure

[step 2] To (E)-[2-(2-propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]-N-hydroxyacetamidine (65 mg, 0.149 mmol) obtained in step 1 was added triethyl orthoformate (1 mL), and the mixture was stirred at 80° C. for 2 hr. The mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 0/100) to give the title compound (compound 9) (28 mg, 42%).

Workup

concentrationThe mixture was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 0/100)

Sources & evidence

ORD record: ord-d9e2a7bdb7db43bea12ca1b95b11097e
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486980B2

Reaction notes

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