HCID 71226800, compound → HCID 136627208, compound

HRID 713514Notes

Reaction equation

HRID 713514 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([CH:13]3[CH2:18][CH2:17][N:16]([CH2:19][C:20](O)=[O:21])[CH2:15][CH2:14]3)=[N:10][N:9]=2)=[CH:4][CH:3]=1.[NH2:23][CH2:24][C:25]1[NH:26][C:27](=[O:35])[C:28]2[CH2:34][O:33][CH2:32][CH2:31][C:29]=2[N:30]=1>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][C:11]([CH:13]3[CH2:14][CH2:15][N:16]([CH2:19][C:20]([NH:23][CH2:24][C:25]4[NH:26][C:27](=[O:35])[C:28]5[CH2:34][O:33][CH2:32][CH2:31][C:29]=5[N:30]=4)=[O:21])[CH2:17][CH2:18]3)=[N:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 71226800HCID 71226800, compoundHCID 1357418942-(Aminomethyl)-7,8-dihydro-3H-pyrano[4,3-D]pyrimidin-4(5H)-one

Product 1

HCID 136627208HCID 136627208, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound (14.8 mg, 0.031 mmol) was prepared following the general procedure of Example 1 from {4-[5-(4-fluoro-phenyl)-[1,3,4]oxadiazol-2-yl]-piperidin-1-yl}-acetic acid (90 mg, 0.206 mmol, 1 eq) and 2-aminomethyl-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one (41.1 mg, 0.227 mmol, 1.1 eq). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.38 (br s, 1H) 8.23-8.26 (m, 1H) 8.05 (dd, J=8.84, 5.31 Hz, 2H) 7.43-7.47 (m, 2H) 4.34 (s, 2H) 4.20 (d, J=5.56 Hz, 2H) 4.04-4.11 (m, 1H) 3.80-3.83 (m, 2H) 3.17 (d, J=5.05 Hz, 2H) 3.03-3.11 (m, 1H) 3.01 (s, 2H) 2.93-2.99 (m, 2H) 2.27-2.33 (m, 2H) 2.05-2.10 (m, 2H) 1.85-2.01 (m, 2H). HR-MS (m/z, MH+): 469.2001, 470.2061. HPLC retention time: 2.66 min (Agilent column 3.0×100 mm 3 um C18 column; flow rate of 1.0 mL/min with gradient from 5% to 95% acetonitrile in 10 min, 0.1% FA).

Sources & evidence

ORD record
ord-32a382b23f4842e589ceebb5d3a43f5f
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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