Formic Acid → HCID 117770270, compound

HRID 1526283Notes

Reaction equation

[C:1](OC(=O)C)(=[O:3])C.C(O)=O.[Br:11][C:12]1[N:17]=[C:16]([CH2:18][NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=2[O:29][CH3:30])[CH:15]=[CH:14][CH:13]=1>O1CCCC1>[Br:11][C:12]1[N:17]=[C:16]([CH2:18][N:19]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=2[O:29][CH3:30])[CH:1]=[O:3])[CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To acetic anhydride (0.703 mL) was added dropwise formic acid (0.349 mL) under ice-cooling, and the mixture was stirred at 55° C. for 45 min. The mixture was allowed to be cooled to room temperature, and tetrahydrofuran (10 mL) was added thereto. A solution of 1-(6-bromopyridin-2-yl)-N-(2,4-dimethoxybenzyl)methanamine obtained in Reference Example 19 (930 mg) in tetrahydrofuran (10 mL) was added dropwise thereto over 3 min under ice-cooling, and the reaction mixture was stirred at room temperature for 30 min. The reaction solution was concentrated under reduced pressure, the obtained colorless oil was subjected to azeotropy with toluene, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (932 mg).

Workup

temperaturecooling
temperatureto be cooled to room temperature
additionwas added dropwise
temperatureover 3 min under ice-cooling
stirringthe reaction mixture was stirred at room temperature for 30 min
concentrationThe reaction solution was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-7549e05cf34649d488bbfa35aee2ab37
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085578B2

Reaction notes

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