1,2,3,4-Tetrahydroisoquinoline → HCID 136237297, compound

HRID 713522Notes

Reaction equation

HRID 713522 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.[CH2:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][CH2:28][NH:27]1>>[O:25]=[C:17]1[NH:16][C:15]([CH2:14][NH:13][C:2](=[O:1])[CH2:3][N:4]2[CH2:9][CH2:8][CH:7]([C:10]([N:27]3[CH2:28][CH2:29][C:30]4[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH2:26]3)=[O:12])[CH2:6][CH2:5]2)=[N:20][C:19]2[CH2:21][CH2:22][O:23][CH2:24][C:18]1=2

Participants

3

Reactant 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 136627188HCID 136627188, compound

Product 1

HCID 136237297HCID 136237297, compoundYield 9.9%

Procedure

The title compound (23 mg) 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 1,2,3,4-tetrahydroisoquinoline (66 mg, 0.50 mmol). 1H NMR (400 MHz, CDC3) δ 8.19 (br. s., 1H), 6.94-7.16 (m, 3H), 4.66 (s, 1H), 4.59 (s, 1H), 4.46 (s, 2H), 4.32 (d, J=5.1 Hz, 2H), 3.85 (t, J=5.3 Hz, 2H), 3.76 (t, J=6.1 Hz, 1H), 3.65 (t, J=5.8 Hz, 1H), 3.40 (br. s., 1H), 3.06 (br. s., 1H), 3.01 (s, 2H), 2.68-2.95 (m, 4H), 2.60 (br. s., 2H), 2.33-2.57 (m, 1H), 2.17 (t, J=11.4 Hz, 2H), 1.87 (dq, J=11.1, 10.9 Hz, 2H). HRMS calculated for C25H31N5O4 466.2454. found (ESI, [M+H]+), 466.2466. Retention time=1.25 min.

Sources & evidence

ORD record
ord-cb475605259541c79b36c3a508c5a80e
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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