Trifluoroacetic acid → 2-[4-(4-Cyclopropylmethoxy-benzoyl)-piperidin-1-yl]-acetic acid

HRID 713526Notes

Reaction equation

HRID 713526 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(CO)CC1.[CH:46]1([CH2:49][O:50][C:51]2[CH:68]=[CH:67][C:54]([C:55]([CH:57]3[CH2:62][CH2:61][N:60]([CH2:63][C:64]([OH:66])=[O:65])[CH2:59][CH2:58]3)=[O:56])=[CH:53][CH:52]=2)[CH2:48][CH2:47]1.[NH2:69][CH2:70][C:71]1[NH:72][C:73](=[O:81])[C:74]2[CH2:80][O:79][CH2:78][CH2:77][C:75]=2[N:76]=1.C(O)(C(F)(F)F)=O>C(#N)C.O>[CH:46]1([CH2:49][O:50][C:51]2[CH:68]=[CH:67][C:54]([C:55]([CH:57]3[CH2:62][CH2:61][N:60]([CH2:63][C:64]([OH:66])=[O:65])[CH2:59][CH2:58]3)=[O:56])=[CH:53][CH:52]=2)[CH2:48][CH2:47]1.[CH:46]1([CH2:49][O:50][C:51]2[CH:52]=[CH:53][C:54]([C:55]([CH:57]3[CH2:58][CH2:59][N:60]([CH2:63][C:64]([NH:69][CH2:70][C:71]4[NH:72][C:73](=[O:81])[C:74]5[CH2:80][O:79][CH2:78][CH2:77][C:75]=5[N:76]=4)=[O:65])[CH2:61][CH2:62]3)=[O:56])=[CH:67][CH:68]=2)[CH2:48][CH2:47]1

Participants

9

Reactant 6

HCID 6422Trifluoroacetic acidHCID 75644CyclopropanemethanolHCID 712264022-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acidHCID 712269532-[4-(4-Cyclopropylmethoxy-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 712269532-[4-(4-Cyclopropylmethoxy-benzoyl)-piperidin-1-yl]-acetic acidHCID 1362373102-[4-(4-Cyclopropylmethoxy-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

2-[4-(4-Cyclopropylmethoxy-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 cyclopropyl-methanol. The title compound (44.7 mg, 0.088 mmol) was prepared following the general procedure of Example 1 from 2-[4-(4-cyclopropylmethoxy-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 481.5 (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=1.27 min. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.26-0.41 (m, 2H), 0.48-0.68 (m, 2H), 1.14-1.29 (m, 1H), 1.65-1.83 (m, 4H), 2.18-2.33 (m, 2H), 2.51 (br. s., 2H), 2.84-3.08 (m, 3H), 3.32 (br. s., 2H), 3.83 (br. s., 2H), 3.91 (d, J=6.06 Hz, 2H), 4.20 (br. s., 2H), 4.34 (br. s., 2H), 7.03 (d, J=7.07 Hz, 2H), 7.94 (d, J=7.58 Hz, 2H), 8.21 (br. s., 1H), 12.38 (br. s., 1H). HRMS calculated for C26H33N4O5: 481.2451 (M+H). found (ESI, [M+H]+): 481.2459.

Sources & evidence

ORD record
ord-e4251f660c5b4be9ab7e2f0f1212b186
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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