Water → HCID 59323453, compound

HRID 2390103Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([CH2:12][CH2:13][CH2:14][NH2:15])[CH:6]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[CH2:5]2.[NH2:24][C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1.C1N=CN([C:36](N2C=NC=C2)=[O:37])C=1.O>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([CH2:12][CH2:13][CH2:14][NH:15][C:36]([NH:24][C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1)=[O:37])[CH:6]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=1)[CH2:5]2

Participants

Conditions

Temperature: 60 °C

Procedure

60 mg of 3-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]propanamine obtained in Example 238-b), 20 mg of 4-aminopyridine, and 34 mg of CDI were dissolved in 1.2 mL of THF, followed by stirring at 60° C. for 3 hours. After completion of the reaction, water was added to the reaction liquid, followed by extraction with chloroform. The organic layer was then washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue obtained was purified using silica gel chromatography (chloroform:methanol=10:1) to obtain 10 mg (yield 12%) of a title compound as a yellow oily substance.

Workup

additionwas added to the reaction liquid
extractionfollowed by extraction with chloroform
washThe organic layer was then washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue obtained
customwas purified

Sources & evidence

ORD record: ord-3549afca0b9e4fe288c76ddf76e9a1f4
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273766B2

Reaction notes

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