Trifluoroacetic acid → {4-[4-(2-Methoxy-ethoxy)-benzoyl]-piperidin-1-yl}-acetic acid

HRID 713528Notes

Reaction equation

HRID 713528 reaction equation
C(OC1C=CC(C(C2CCN(CC(O)=O)CC2)=O)=CC=1)C.FC1C=CC(C(C2CCN(CC(O)=O)CC2)=O)=CC=1.[CH3:41][O:42][CH2:43][CH2:44][O:45][C:46]1[CH:63]=[CH:62][C:49]([C:50]([CH:52]2[CH2:57][CH2:56][N:55]([CH2:58][C:59]([OH:61])=[O:60])[CH2:54][CH2:53]2)=[O:51])=[CH:48][CH:47]=1.[NH2:64][CH2:65][C:66]1[NH:67][C:68](=[O:76])[C:69]2[CH2:75][O:74][CH2:73][CH2:72][C:70]=2[N:71]=1.C(O)(C(F)(F)F)=O>C(#N)C.O.COCCO>[CH3:41][O:42][CH2:43][CH2:44][O:45][C:46]1[CH:47]=[CH:48][C:49]([C:50]([CH:52]2[CH2:57][CH2:56][N:55]([CH2:58][C:59]([OH:61])=[O:60])[CH2:54][CH2:53]2)=[O:51])=[CH:62][CH:63]=1.[CH3:41][O:42][CH2:43][CH2:44][O:45][C:46]1[CH:47]=[CH:48][C:49]([C:50]([CH:52]2[CH2:53][CH2:54][N:55]([CH2:58][C:59]([NH:64][CH2:65][C:66]3[NH:67][C:68](=[O:76])[C:69]4[CH2:75][O:74][CH2:73][CH2:72][C:70]=4[N:71]=3)=[O:61])[CH2:56][CH2:57]2)=[O:51])=[CH:62][CH:63]=1

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 712264022-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acidHCID 71227165{4-[4-(2-Methoxy-ethoxy)-benzoyl]-piperidin-1-yl}-acetic acidHCID 712274202-(4-(4-Ethoxybenzoyl)piperidin-1-yl)acetic acidHCID 1357418942-(Aminomethyl)-7,8-dihydro-3H-pyrano[4,3-D]pyrimidin-4(5H)-one

Product 2

HCID 71227165{4-[4-(2-Methoxy-ethoxy)-benzoyl]-piperidin-1-yl}-acetic acidHCID 1362373232-{4-[4-(2-Methoxy-ethoxy)-benzoyl]-piperidin-1-yl}-N-(4-oxo-3,5,7,8-tetrahydro-4H-pyrano[4,3-d]pyrimidin-2-ylmethyl)-acetamide

Reagents, catalysts & solvents 2

HCID 80192-MethoxyethanolSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

{4-[4-(2-Methoxy-ethoxy)-benzoyl]-piperidin-1-yl}-acetic acid was prepared following the general procedures for the synthesis of 2-(4-(4-ethoxybenzoyl)piperidin-1-yl)acetic acid from 2-(4-(4-fluorobenzoyl)piperidin-1-yl)acetic acid and 2-methoxy-ethanol. The title compound (190 mg, 0.373 mmol) was prepared following the general procedure of Example 1 from {4-[4-(2-methoxy-ethoxy)-benzoyl]-piperidin-1-yl}-acetic acid and 2-aminomethyl-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one. MS (ESI) m/z 484.8 (M+H+); HPLC (Insertsil ODS3 100×3 mm C-18 column: mobile phase: 5-95% acetonitrile/water with 0.1% TFA, at 1 mL/min over 7.75 min.) t=1.46 min. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.51-1.83 (m, 6H), 2.20-2.33 (m, 2H), 2.51 (br. s., 2H), 2.92-3.03 (m, 4H), 3.24-3.41 (m, 4H), 3.65-3.71 (m, 2H), 3.82 (t, J=5.31 Hz, 2H), 4.16-4.24 (m, 2H), 4.34 (s, 2H), 7.05 (d, J=8.59 Hz, 2H), 7.95 (d, J=8.59 Hz, 2H), 8.24 (br. s., 1H), 12.38 (br. s., 1H). HRMS calculated for C25H33N4O6: 485.2400 (M+H). found (ESI, [M+H]+): 485.2394.

Sources & evidence

ORD record
ord-b2308155067848bfa841eed89c9637f5
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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