Triethylamine → HCID 49841774, compound

HRID 1968178Notes

Reaction equation

[CH3:1][C:2]1([N:8]2[CH2:17][C:16]3=[CH:18][NH:19][C:14]4[C:15]3=[C:10]([CH:11]=[CH:12][N:13]=4)[C:9]2=[O:20])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[C:28]([CH2:30][C:31](ON1C(=O)CCC1=O)=[O:32])#[N:29]>CCO>[CH3:1][C:2]1([N:8]2[CH2:17][C:16]3=[CH:18][NH:19][C:14]4[C:15]3=[C:10]([CH:11]=[CH:12][N:13]=4)[C:9]2=[O:20])[CH2:7][CH2:6][N:5]([C:31](=[O:32])[CH2:30][C:28]#[N:29])[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

4-(4-Methylpiperidin-4-yl)-3,4-dihydropyrrolo[4,3,2-de][2,6]naphthyridin-5(1H)-one (21 mg, 0.078 mmol) and triethylamine (0.032 mL, 0.233 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 (17 mg, 0.093 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 40% B in A and gave 13 mg of the title compound as its TFA salt. 1H NMR (400 MHz, CD3OD) δ 7.61 (m, 1H), 7.43 (m, 1H), 5.08 (s, 2H), 3.90 (m, 2H), 3.72 (m, 1H), 3.61-3.62 (m, 1H), 3.51-3.52 (m, 2H), 2.65-2.69 (m, 1H), 2.51-2.57 (m, 1H), 2.22-2.26 (m, 1H), 2.10-2.12 (m, 1H), 1.66 (s, 3H). [M+H] found 338.

Workup

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

Sources & evidence

ORD record: ord-63bf17f56b504304a754f5f3997d0a1f
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420816B2

Reaction notes

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