Dichloromethane → HCID 46929235, compound

HRID 1514735Notes

Reaction equation

CO[C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([CH2:19][CH2:20][CH2:21][CH3:22])=[N:14][O:15][C:16]=2[CH2:17][OH:18])=[N:6][CH:5]=1.[CH:24]([NH2:27])([CH3:26])[CH3:25].N12CCCNC1=NCCC2.ClCCl>C1(C)C=CC=CC=1>[CH2:19]([C:13]1[C:12]([CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([NH:27][CH:24]([CH3:26])[CH3:25])=[O:23])=[CH:5][N:6]=2)=[C:16]([CH2:17][OH:18])[O:15][N:14]=1)[CH2:20][CH2:21][CH3:22]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 6-[3-butyl-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (100 mg, 0.31 mmol) in toluene (1 mL) was added isopropylamine (55 mg, 0.93 mmol) and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (26 mg, 0.19 mmol). The reaction mixture was stirred for 3.5 days at 50° C. A further portion of isopropylamine was added and the reaction was heated at 50° C. for an additional 3.5 days. Dichloromethane (40 mL) was added and the reaction mixture was concentrated in vacuo onto silica gel and purified by chromatography (silica, dichloromethane:methanol 1:0 to 9:1) to afford the title compound (18 mg, 17%) as a colorless oil. MS: m/e=348.3 [M+H]+.

Workup

temperaturethe reaction was heated at 50° C. for an additional 3.5 days
concentrationthe reaction mixture was concentrated in vacuo onto silica gel
custompurified by chromatography (silica, dichloromethane:methanol 1:0 to 9:1)

Sources & evidence

ORD record: ord-ada584b328e84d3ba710b18b5f039e20
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222246B2

Reaction notes

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