Triethylamine → HCID 49841777, compound

HRID 1968182Notes

Reaction equation

[CH2:1]([C:3]1([N:9]2[CH2:18][C:17]3=[CH:19][NH:20][C:15]4[C:16]3=[C:11]([CH:12]=[CH:13][N:14]=4)[C:10]2=[O:21])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)[CH3:2].C(N(CC)CC)C.[C:29]([CH2:31][C:32](ON1C(=O)CCC1=O)=[O:33])#[N:30]>CCO>[CH2:1]([C:3]1([N:9]2[CH2:18][C:17]3=[CH:19][NH:20][C:15]4[C:16]3=[C:11]([CH:12]=[CH:13][N:14]=4)[C:10]2=[O:21])[CH2:8][CH2:7][N:6]([C:32](=[O:33])[CH2:31][C:29]#[N:30])[CH2:5][CH2:4]1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

4-(4-Ethylpiperidin-4-yl)-3,4-dihydropyrrolo[4,3,2-de][2,6]naphthyridin-5(1H)-one (25 mg, 0.088 mmol) and triethylamine (0.037 mL, 0.264 mmol) were dissolved in EtOH (3 mL) and cooled to 0° C. and allowed to stir for 10 min. Then 2,5-dioxopyrrolidin-1-yl 2-cyanoacetate (19 mg, 0.106 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 10% to 50% B in A and gave 16 mg of the title compound as its TFA salt. 1H NMR (400 MHz, CD3OD) δ 7.03 (m, 1H), 6.86 (m, 1H), 4.53 (d, 2H, J=2.0 Hz), 3.08-3.11 (m, 2H), 2.93-2.94 (m, 2H), 2.72-2.73 (m, 2H), 2.04-2.09 (m, 1H), 1.91-1.94 (m, 1H), 1.36-1.72 (m, 4H), 0.35 (t, 3H, J=7.6 Hz). [M+H] found 352.

Workup

additionwas added dropwise
stirringto stir for 30 min at 0° C
concentrationThe solution was concentrated in vacuo
custompurified via preparative HPLC 10% to 50% B in A

Sources & evidence

ORD record: ord-2b0cbf695723441cae8d8c096a7c85a3
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420816B2

Reaction notes

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