Triethylamine → 3-oxo-3-(4-(5-oxopyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)piperidin-1-yl)propanenitrile

HRID 1968174Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH2:16][C:15]3=[CH:17][NH:18][C:13]4[C:14]3=[C:9]([CH:10]=[CH:11][N:12]=4)[C:8]2=[O:19])[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:27]([CH2:29][C:30](ON1C(=O)CCC1=O)=[O:31])#[N:28]>CCO>[O:31]=[C:30]([N:1]1[CH2:2][CH2:3][CH:4]([N:7]2[CH2:16][C:15]3=[CH:17][NH:18][C:13]4[C:14]3=[C:9]([CH:10]=[CH:11][N:12]=4)[C:8]2=[O:19])[CH2:5][CH2:6]1)[CH2:29][C:27]#[N:28]

Participants

Conditions

Temperature: 0 °C

Procedure

4-(Piperidin-4-yl)-3,4-dihydropyrrolo[4,3,2-de][2,6]naphthyridin-5(1H)-one (34 mg, 0.133 mmol) and triethylamine (0.055 mL, 0.398 mmol) were dissolved in EtOH (4 mL) and cooled to 0° C. and allowed to stir for 10 min. Then 2,5-dioxopyrrolidin-1-yl 2-cyanoacetate (29 mg, 0.159 mmol) dissolved in EtOH (1 mL) was added dropwise and the mixture was allowed to stir for 30 min at 0° C. The solution was concentrated in vacuo and purified via preparative HPLC eluting with 10% to 40% B in A and gave 10 mg of the title compound as its TFA salt. 1H NMR (400 MHz, CD3OD) δ 7.60 (m, 1H), 7.43 (m, 1H), 4.98 (s, 2H), 4.84-4.88 (m, 1H), 4.68-4.72 (m, 1H), 3.89-3.95 (m, 3H), 3.33 (m, 1H), 2.80-2.88 (m, 1H), 1.86-2.05 (m, 4H). [M+H] found 324.

Workup

additionwas added dropwise
stirringto stir for 30 min at 0° C
concentrationThe solution was concentrated in vacuo
custompurified via preparative HPLC
washeluting with 10% to 40% B in A

Sources & evidence

ORD record: ord-26947276a4e9411d8af5625551ad7991
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420816B2

Reaction notes

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