1-(2-Fluorophenyl)piperidin-4-one → N-[2-({(3R)-1-[1-(2-fluorophenyl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide

HRID 564373Notes

Reaction equation

HRID 564373 reaction equation
COC1N=CC(N2CCC([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)CC2)=CC=1.[F:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[N:44]1[CH2:49][CH2:48][C:47](=O)[CH2:46][CH2:45]1.COC1N=CC(N2CCC(=O)CC2)=CC=1>>[F:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[N:44]1[CH2:49][CH2:48][CH:47]([N:15]2[CH2:19][CH2:18][C@@H:17]([NH:20][C:21](=[O:36])[CH2:22][NH:23][C:24](=[O:35])[C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:32])([F:34])[F:33])[CH:26]=3)[CH2:16]2)[CH2:46][CH2:45]1

Participants

4

Reactant 3

HCID 111168931-(2-Fluorophenyl)piperidin-4-oneHCID 16722463N-[2-({(3R)-1-[1-(6-methoxypyridin-3-yl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamideHCID 220002791-(6-Methoxypyridin-3-yl)piperidin-4-one

Product 1

HCID 57814111N-[2-({(3R)-1-[1-(2-fluorophenyl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide

Procedure

The title compound 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-(2-fluorophenyl)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: 1.86-1.92 (m, 2H), 2.03-2.22 (m, 3H), 2.41-2.48 (m, 1H), 2.75 (t, J=11.1 Hz, 2H), 3.16-3.26 (m, 1H), 3.36-3.44 (m, 2H), 3.54-3.66 (m, 4H), 4.04 (s, 2H), 4.51-4.55 (m, 1H), 6.96-7.10 (m, 4H), 7.70 (t, J=7.6 Hz, 2H), 7.87 (d, J=8.4 Hz, 1H), 8.15 (d, J=7.5 Hz, 1H), 8.22 (s, 1H), 8.36 (s, 2H). MS m/z: 493 (M+1)

Workup

  1. customwas isolated as a white solid

Sources & evidence

ORD record
ord-bb68b665c083483e8d88526a3ebe13c5
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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