Trifluoroacetic acid → 2-(4-(4-Propoxybenzoyl)piperidin-1-yl)acetic acid

HRID 713525Notes

Reaction equation

HRID 713525 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.[CH2:41]([O:44][C:45]1[CH:62]=[CH:61][C:48]([C:49]([CH:51]2[CH2:56][CH2:55][N:54]([CH2:57][C:58]([OH:60])=[O:59])[CH2:53][CH2:52]2)=[O:50])=[CH:47][CH:46]=1)[CH2:42][CH3:43].[NH2:63][CH2:64][C:65]1[NH:66][C:67](=[O:75])[C:68]2[CH2:74][O:73][CH2:72][CH2:71][C:69]=2[N:70]=1.C(O)(C(F)(F)F)=O>C(#N)C.O.C(O)CC>[CH2:41]([O:44][C:45]1[CH:46]=[CH:47][C:48]([C:49]([CH:51]2[CH2:56][CH2:55][N:54]([CH2:57][C:58]([OH:60])=[O:59])[CH2:53][CH2:52]2)=[O:50])=[CH:61][CH:62]=1)[CH2:42][CH3:43].[O:75]=[C:67]1[NH:66][C:65]([CH2:64][NH:63][C:58](=[O:60])[CH2:57][N:54]2[CH2:53][CH2:52][CH:51]([C:49](=[O:50])[C:48]3[CH:47]=[CH:46][C:45]([O:44][CH2:41][CH2:42][CH3:43])=[CH:62][CH:61]=3)[CH2:56][CH2:55]2)=[N:70][C:69]2[CH2:71][CH2:72][O:73][CH2:74][C:68]1=2

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 712264022-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acidHCID 712269132-(4-(4-Propoxybenzoyl)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 712269132-(4-(4-Propoxybenzoyl)piperidin-1-yl)acetic acidHCID 136237309N-(4-Oxo-3,5,7,8-tetrahydro-4H-pyrano[4,3-d]pyrimidin-2-ylmethyl)2-[4-(4-propoxy-benzoyl)-piperidin-1-yl]acetamide

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

2-(4-(4-Propoxybenzoyl)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 propan-1-ol. The title compound (76.1 mg, 0.15 mmol) was prepared following the general procedure of Example 1 from 2-(4-(4-propoxybenzoyl)piperidin-1-yl)acetic acid and 2-aminomethyl-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one. MS (ESI) m/z 469.4 (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=1.39 min. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.99 (t, 3H), 1.60-1.88 (m, 6H), 2.14-2.33 (m, 2H), 2.43-2.65 (m, 4H), 2.98 (br. s., 2H), 3.23-3.42 (m, 1H), 3.83 (br. s., 2H), 3.95-4.10 (m, 2H), 4.20 (br. s., 2H), 4.34 (br. s., 2H), 7.03 (d, J=4.55 Hz, 2H), 7.95 (d, J=4.55 Hz, 2H), 8.22 (br. s., 1H), 12.38 (br. s., 1H). HRMS calculated for C26H33N4O6: 469.2451 (M+H). found (ESI, [M+H]+): 469.2459.

Sources & evidence

ORD record
ord-8e1ef33e039640f4a6bada625135596a
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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