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

HRID 713529Notes

Reaction equation

HRID 713529 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.C1(CCO)CC1.[CH:47]1([CH2:50][CH2:51][O:52][C:53]2[CH:70]=[CH:69][C:56]([C:57]([CH:59]3[CH2:64][CH2:63][N:62]([CH2:65][C:66]([OH:68])=[O:67])[CH2:61][CH2:60]3)=[O:58])=[CH:55][CH:54]=2)[CH2:49][CH2:48]1.[NH2:71][CH2:72][C:73]1[NH:74][C:75](=[O:83])[C:76]2[CH2:82][O:81][CH2:80][CH2:79][C:77]=2[N:78]=1.C(O)(C(F)(F)F)=O>C(#N)C.O>[CH:47]1([CH2:50][CH2:51][O:52][C:53]2[CH:70]=[CH:69][C:56]([C:57]([CH:59]3[CH2:60][CH2:61][N:62]([CH2:65][C:66]([OH:68])=[O:67])[CH2:63][CH2:64]3)=[O:58])=[CH:55][CH:54]=2)[CH2:49][CH2:48]1.[CH:47]1([CH2:50][CH2:51][O:52][C:53]2[CH:70]=[CH:69][C:56]([C:57]([CH:59]3[CH2:60][CH2:61][N:62]([CH2:65][C:66]([NH:71][CH2:72][C:73]4[NH:74][C:75](=[O:83])[C:76]5[CH2:82][O:81][CH2:80][CH2:79][C:77]=5[N:78]=4)=[O:68])[CH2:63][CH2:64]3)=[O:58])=[CH:55][CH:54]=2)[CH2:48][CH2:49]1

Participants

9

Reactant 6

HCID 6422Trifluoroacetic acidHCID 1376422-Cyclopropylethan-1-olHCID 712264022-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acidHCID 71226568{4-[4-(2-Cyclopropyl-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 71226568{4-[4-(2-Cyclopropyl-ethoxy)-benzoyl]-piperidin-1-yl}-acetic acidHCID 1362373242-{4-[4-(2-Cyclopropyl-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 1

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

Procedure

{4-[4-(2-Cyclopropyl-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-cyclopropyl-ethanol. The title compound (74.3 mg, 0.143 mmol) was prepared following the general procedure of Example 1 from {4-[4-(2-cyclopropyl-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 495.5 (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=1.51 min. 1H NMR (400 MHz, DMSO-d6) δ ppm −0.07-0.05 (m, 2H), 0.23-0.36 (m, 2H), 0.58-0.75 (m, 1H), 1.47-1.65 (m, 6H), 2.01-2.18 (m, 2H), 2.37 (br. s., 2H), 2.78-2.89 (m, 3H), 3.20 (dd, J=15.41, 6.32 Hz, 2H), 3.69 (t, J=5.56 Hz, 2H), 3.98 (t, J=6.57 Hz, 2H), 4.05 (d, J=5.56 Hz, 2H), 4.20 (s, 2H), 6.90 (d, J=9.09 Hz, 2H), 7.81 (d, J=8.59 Hz, 2H), 8.08 (t, J=5.81 Hz, 1H), 12.24 (br. s., 1H). HRMS calculated for C27H35N4O5: 495.2607 (M+H). found (ESI, [M+H]+): 495.2622.

Sources & evidence

ORD record
ord-cf173056d3d5457b9d3fc748fe1db440
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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