N-[2-({(3R)-1-[1-(6-methoxypyridin-3-yl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide → N-[2-({(3R)-1-[1-(4-methoxyphenyl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide

HRID 564368Notes

Reaction equation

HRID 564368 reaction equation
[CH3:1][O:2][C:3]1N=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[CH2:19][CH2:18][C@@H:17]([NH:20][C:21](=[O:36])[CH2:22][NH:23][C:24](=[O:35])[C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=4)[CH2:16]3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[CH3:37]OC1C=CC(N2CCC(=O)CC2)=CC=1.COC1N=CC(N2CCC(=O)CC2)=CC=1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:10][CH2:11][CH:12]([N:15]3[CH2:19][CH2:18][C@@H:17]([NH:20][C:21](=[O:36])[CH2:22][NH:23][C:24](=[O:35])[C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:32])([F:34])[F:33])[CH:26]=4)[CH2:16]3)[CH2:13][CH2:14]2)=[CH:7][CH:37]=1

Participants

4

Reactant 3

HCID 16722463N-[2-({(3R)-1-[1-(6-methoxypyridin-3-yl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamideHCID 212605551-(4-Methoxyphenyl)piperidin-4-oneHCID 220002791-(6-Methoxypyridin-3-yl)piperidin-4-one

Product 1

HCID 57814067N-[2-({(3R)-1-[1-(4-methoxyphenyl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide

Procedure

N-[2-({(3R)-1-[1-(4-methoxyphenyl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide was synthesized in similar fashion to N-[2-({(3R)-1-[1-(6-methoxypyridin-3-yl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide whereby 1-(4-methoxyphenyl)piperidin-4-one was substituted for 1-(6-methoxypyridin-3-yl)piperidin-4-one, and was isolated as a white solid. 1H-NMR (CD3OD) δ: 1.82-1.89 (m, 2H), 2.17-2.21 (m, 3H), 2.43-2.46 (m, 1H), 2.68 (q, J=11.7 Hz, 2H), 3.17-3.25 (ma 1H), 3.38-3.46 (m, 2H), 3.57-3.66 (m, 4H), 3.72 (s, 3H), 4.04 (s, 2H), 4.50-4.52 (m, 1H), 6.80-6.85 (m, 2H); 6.92-6.96 (m, 2H), 7.69 (t, J=7.9 Hz, 1H), 7.87 (d, J=8.1 Hz, 1H), 8.15 (d, J=7.8 Hz, 1H), 8.22 (s, 1H), 8.29 (s, 2H). MS m/z: 505 (M+1).

Workup

  1. customwas isolated as a white solid

Sources & evidence

ORD record
ord-c6b2e81abdd14d6e82858985b22ab744
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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