Quinoline, 1,2,3,4-tetrahydro-6-methoxy- → HCID 136237298, compound

HRID 713523Notes

Reaction equation

HRID 713523 reaction equation
[O:1]=[C:2]([NH:13][CH2:14][C:15]1[NH:16][C:17](=[O:25])[C:18]2[CH2:24][O:23][CH2:22][CH2:21][C:19]=2[N:20]=1)[CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]([OH:12])=O)[CH2:6][CH2:5]1.[CH3:26][O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[NH:34][CH2:33][CH2:32][CH2:31]2>>[CH3:26][O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[N:34]([C:10]([CH:7]1[CH2:8][CH2:9][N:4]([CH2:3][C:2]([NH:13][CH2:14][C:15]3[NH:16][C:17](=[O:25])[C:18]4[CH2:24][O:23][CH2:22][CH2:21][C:19]=4[N:20]=3)=[O:1])[CH2:5][CH2:6]1)=[O:12])[CH2:33][CH2:32][CH2:31]2

Participants

3

Reactant 2

HCID 67113Quinoline, 1,2,3,4-tetrahydro-6-methoxy-HCID 136627188HCID 136627188, compound

Product 1

HCID 136237298HCID 136237298, compoundYield 22.6%

Procedure

The title compound (56 mg, 22% yield) was prepared following the general procedure of Example 1 from 1-(2-oxo-2-((4-oxo-4,5,7,8-tetrahydro-3H-pyrano[4,3-d]pyrimidin-2-yl)methylamino)ethyl)piperidine-4-carboxylic acid (250 mg, 0.50 mmol) and 6-methoxy-1,2,3,4-tetrahydroquinoline (82 mg, 0.50 mmol). 1H NMR (400 MHz, CDC3) δ 10.68 (br. s., 1H), 8.12 (br. s, 0.5H), 6.97 (br. s., 0.5H), 6.73-6.80 (m, 2H), 4.58 (s, 2H), 4.38 (d, J=5.6 Hz, 2H), 3.97 (t, J=5.6 Hz, 2H), 3.63-3.89 (m, 5H), 3.10 (br. s., 2H), 2.89 (br. s., 3H), 2.71 (t, J=5.3 Hz, 4H), 2.15 (br. s., 2H), 1.82-2.09 (m, 5H), 1.68 (br. s., 1H). HRMS calculated for C26H33N5O5 496.2560. found (ESI, [M+H]+), 496.2561. Retention time=1.29 min.

Sources & evidence

ORD record
ord-15376b642d65426eb055be8473238679
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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