Triethylamine → HCID 178480737, compound

HRID 2236845Notes

Reaction equation

[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]/OC.[NH2:17][C:18]1[C:19]([OH:31])=[N:20][C:21]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[CH:22][CH:23]=1.C(N(CC)CC)C>CN(C)C=O>[OH:31][C:19]1[C:18]([NH:17]/[CH:14]=[C:5]2\[C:6](=[O:13])[NH:7][C:8](=[O:12])[C:9]3[C:4]\2=[CH:3][C:2]([I:1])=[CH:11][CH:10]=3)=[CH:23][CH:22]=[C:21]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)[N:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

(4E)-6-iodo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (0.12 g, 0.35 mmol), 3-amino-6-(4-methyl-piperazin-1-yl)-pyridin-2-ol (0.15 g, contaminated with triethylammonium trifluoroacetate) were coupled in N,N-dimethylformamide (3 mL) with triethylamine (0.27 mL). The mixture is heated in a 100° C. oil bath for three hours. The reaction mixture is purified by reverse phase HPLC to give (4Z)-4-({[2-hydroxy-6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino}methylene)-6-iodoisoquinoline-1,3(2H,4H)-dione.2 trifluoroacetic acid salt (18 mg, 7.0%).

Workup

customThe reaction mixture is purified by reverse phase HPLC

Sources & evidence

ORD record: ord-8e695cd8efaa401a889fd70a8df81a9f
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713994B2

Reaction notes

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