Hydrochloric Acid → HCID 71737074, compound

HRID 1481058Notes

Reaction equation

CO[C:3]([C:5]1[N:6]=[C:7]([C:23]#[N:24])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].Cl.[NH2:26][C@@H:27]([CH:32]([CH3:34])[CH3:33])[CH2:28][C:29]([OH:31])=[O:30].C[O-].[Na+].Cl>COCCO>[C:23]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:9]=2)[C:14]([OH:15])=[C:5]([C:3]([NH:26][CH:27]([CH:32]([CH3:34])[CH3:33])[CH2:28][C:29]([OH:31])=[O:30])=[O:4])[N:6]=1)#[N:24]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (50 mg, 0.16 mmole), (R)-3-amino-4-methylpentanoic acid hydrochloride (52 mg, 0.31 mmole) (Chem-Impex International Inc., Wood Dale Ill.), and sodium methoxide (25 mg, 0.46 mmole) in 2-methoxyethanol was stirred at 130° C. for two hours before it was cooled to room temperature and acidified with 1 N HCl. The mixture was partitioned between dichloromethane and water. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of 1% acetic acid, ethyl acetate and hexanes to give the title compound as a yellow solid (9 mg): MS: (+) m/z 420.06 (M+1), (−) m/z 418.02 (M−1).

Workup

temperaturewas cooled to room temperature
customThe mixture was partitioned between dichloromethane and water
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography on silica gel with a gradient of 1% acetic acid, ethyl acetate and hexanes

Sources & evidence

ORD record: ord-9c33426826a14dd19cea39ca411c04e7
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409892B2

Reaction notes

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