Hydrochloric Acid → HCID 71735459, compound

HRID 1481237Notes

Reaction equation

Cl.[NH2:2][CH2:3][CH:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[F:14])[C:5]([OH:7])=[O:6].C[O:16][C:17]([C:19]1[N:20]=[CH:21][C:22]2[C:27]([C:28]=1[OH:29])=[CH:26][CH:25]=[C:24]([O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH:23]=2)=O.C1CCN2[C:40](=[N:41]CCC2)CC1>CC(N(C)C)=O>[C:40]([C:21]1[C:22]2[C:27](=[CH:26][CH:25]=[C:24]([O:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:23]=2)[C:28]([OH:29])=[C:19]([C:17]([NH:2][CH2:3][CH:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])[C:5]([OH:7])=[O:6])=[O:16])[N:20]=1)#[N:41]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of HCl salt of 3-amino-2-(2-fluoro-phenyl)-propionic acid (82 mg), 4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (40 mg) and DBU (0.112 mL) in DMA (1 mL) was heated in an oil bath (150° C.) for 1 h. The reaction mixture was then partitioned between EtOAc and diluted HCl solution, EtOAc phase was separated and washed with water, diluted NaCl solution and dried over anhydrous sodium sulfate solution, filtered, concentrated and silica gel column purified to give desired product (40 mg). LC-MS ESI+: 472 (M+1)+.

Workup

customThe reaction mixture was then partitioned between EtOAc and diluted HCl solution, EtOAc phase
customwas separated
washwashed with water, diluted NaCl solution
dry with materialdried over anhydrous sodium sulfate solution
filtrationfiltered
concentrationconcentrated
customsilica gel column purified

Sources & evidence

ORD record: ord-0791816922e94eafa28dec9fee90340d
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409892B2

Reaction notes

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