HCID 71227054, compound → HCID 136627209, compound

HRID 713515Notes

Reaction equation

HRID 713515 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([CH:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]([OH:23])=O)[CH2:16][CH2:15]3)=[N:11][N:10]=2)=[CH:5][CH:4]=1.[NH2:24][CH2:25][C:26]1[NH:27][C:28](=[O:36])[C:29]2[CH2:35][O:34][CH2:33][CH2:32][C:30]=2[N:31]=1>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][C:12]([CH:14]3[CH2:15][CH2:16][N:17]([CH2:20][C:21]([NH:24][CH2:25][C:26]4[NH:27][C:28](=[O:36])[C:29]5[CH2:35][O:34][CH2:33][CH2:32][C:30]=5[N:31]=4)=[O:23])[CH2:18][CH2:19]3)=[N:11][N:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 71227054HCID 71227054, compoundHCID 1357418942-(Aminomethyl)-7,8-dihydro-3H-pyrano[4,3-D]pyrimidin-4(5H)-one

Product 1

HCID 136627209HCID 136627209, compoundYield 7.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound (10 mg, 0.018 mmol) was prepared following the general procedure of Example 1 from {4-[5-(4-methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-piperidin-1-yl}-acetic acid (100 mg, 0.246 mmol, 1.0 eq) and 2-aminomethyl-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one (46.8 mg, 0.258 mmol, 1.05 eq). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.43 (br s, 1H) 8.27 (br s, 1H) 7.92 (d, J=9.03 Hz, 2H) 7.14 (d, J=9.03 Hz, 2H) 4.34 (s, 2H) 4.20 (d, J=5.52 Hz, 2H) 3.73-3.92 (m, 5H) 2.86-3.11 (m, 5H) 2.18-2.36 (m, 2H) 2.01-2.10 (m, 2H) 1.87-1.98 (m, 2H). HR-MS (m/z, MH+): 481.2205, 482.2262. HPLC retention time: 2.69 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-a2ed356dc614460b8d6de4ea223a5b8f
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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