Triethylamine → HCID 44453586, compound

HRID 1989032Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11](Cl)=[N:12][CH:13]=2)[N:8]([C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[CH2:23][CH2:22][CH2:21]3)[CH:7]=1)=O)C.[CH3:27][N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH:35]=2)[CH2:30][CH2:29]1.C([N:43](CC)CC)C>CN1C(=O)CCC1>[CH2:23]1[C:24]2[C:20](=[CH:19][C:18]([N:8]3[C:9]4[C:14](=[CH:13][N:12]=[C:11]([NH:40][C:37]5[CH:38]=[CH:39][C:34]([N:31]6[CH2:30][CH2:29][N:28]([CH3:27])[CH2:33][CH2:32]6)=[CH:35][CH:36]=5)[CH:10]=4)[C:15](=[O:16])[C:6]([C:4]([NH2:43])=[O:3])=[CH:7]3)=[CH:26][CH:25]=2)[CH2:21][CH2:22]1

Participants

Conditions

Temperature: 200 °C

Procedure

To a solution of 7-chloro-1-indan-5-yl-4-oxo-1,4-dihydro-[1,6]naphthyridine-3-carboxylic acid ethyl ester (40 mg, 0.11 mmol) and 4-(4-Methyl-piperazin-1-yl)-phenylamine (45 mg, 0.23 mmol) in 1 mL of NMP was added triethylamine (24 mg, 0.24 mmol). The reaction was heated in a microwave reactor at 200° C. for 2 hours. The solvent was evaporated under vacuo and the product was purified by preparative HPLC (32 mL/min, 5-100% H2O/MeCN (0.01% TFA, v/v) gradient over 15 min). The title compound was obtained as a yellow solid (6.9 mg, 10%). 1H NMR (400 MHz, CD3OD) δ (ppm): 9.11 (s, 1H), 8.57 (s, 1H), 7.45 (d, J=7.9 Hz, 1H), 7.35 (m, 3H), 7.25 (dd, J=1.9 Hz, J=7.9 Hz, 1H), 6.96 (d, J=8.8 Hz, 2H), 6.13 (s, 1H), 3.40-3.80 (br, 8H), 3.01 (m, 4H), 2.96 (s, 3H), 2.17 (m, 2H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C29H30N6O2: 495.24 (M+H), Found: 495.1.

Workup

customThe solvent was evaporated under vacuo
customthe product was purified by preparative HPLC (32 mL/min, 5-100% H2O/MeCN (0.01% TFA, v/v) gradient over 15 min)

Sources & evidence

ORD record: ord-17348d3280b04e65b146c695fc9b87d0
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642270B2

Reaction notes

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