1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 89813051, compound

HRID 1481216Notes

Reaction equation

[C:1]([O:5][C:6](=[O:16])[CH:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:8][NH2:9])([CH3:4])([CH3:3])[CH3:2].C[O:18][C:19]([C:21]1[N:22]=[C:23]([C:39]#[N:40])[C:24]2[C:29]([C:30]=1[OH:31])=[CH:28][CH:27]=[C:26]([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH:25]=2)=O.C1CCN2C(=NCCC2)CC1>CC(N(C)C)=O>[C:1]([O:5][C:6](=[O:16])[CH:7]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:8][NH:9][C:19]([C:21]1[N:22]=[C:23]([C:39]#[N:40])[C:24]2[C:29]([C:30]=1[OH:31])=[CH:28][CH:27]=[C:26]([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH:25]=2)=[O:18])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 3-amino-2-phenyl-propionic acid tert-butyl ester (108 mg), 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (52 mg) and DBU (0.036 mL) in DMA (0.5 mL) was heated in an oil bath (150° C.) for 1.5 h. After cooling, the reaction mixture was partitioned between EtOAc and diluted HCl solution; EtOAc phase was separated and washed with water, diluted NaCl solution respectively and dried over anhydrous sodium sulfate solution, filtered, concentrated and silica gel column purified to give desired product as brown solid (60 mg). LC-MS ESI+: 510 (M+1)+.

Workup

temperatureAfter cooling
customthe reaction mixture was partitioned between EtOAc and diluted HCl solution
customEtOAc phase was separated
washwashed with water, diluted NaCl solution respectively
dry with materialdried over anhydrous sodium sulfate solution
filtrationfiltered
concentrationconcentrated
customsilica gel column purified

Sources & evidence

ORD record: ord-bee45bb7d52c43b592b65487e02a2d25
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409892B2

Reaction notes

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