Ethyl orthoformate → HCID 67210516, compound

HRID 452135Notes

Reaction equation

[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:29]=[CH:28][C:13]3/[C:14](=[CH:23]/[C:24]([NH:26][NH2:27])=[O:25])/[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:30]=[CH:31][CH:32]=[CH:33][C:6]=2[N:5]=1)[CH2:2][CH3:3].[CH:34](OCC)(OCC)OCC>>[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:29]=[CH:28][C:13]3/[C:14](=[CH:23]/[C:24]4[O:25][CH:34]=[N:27][N:26]=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:30]=[CH:31][CH:32]=[CH:33][C:6]=2[N:5]=1)[CH2:2][CH3:3]

Participants

Reactant 2

HCID 31214Ethyl orthoformate

HCID 67210662HCID 67210662, compound

Product 1

HCID 67210516HCID 67210516, compoundYield 93%

Conditions

Temperature: 120 °C

Procedure

To (E)-[2-(2-propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetohydrazide (27 mg, 0.062 mmol) obtained in Example 7, step 1 was added triethyl orthoformate (0.5 mL), and the mixture was stirred at 120° C. for 20 hr. The mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30 to 0/100) to give the title compound (compound 11) (26 mg, 93%).

Workup

concentrationThe mixture was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30 to 0/100)

Sources & evidence

ORD record: ord-e4feb03edb4d4110957b81607fed216a
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486980B2

Reaction notes

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