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-(3-chlorophenyl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide

HRID 564361Notes

Reaction equation

HRID 564361 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.[Cl:37][C:38]1[CH:39]=[C:40]([N:44]2[CH2:49][CH2:48][C:47](=O)[CH2:46][CH2:45]2)[CH:41]=[CH:42][CH:43]=1.COC1N=CC(N2CCC(=O)CC2)=CC=1>>[Cl:37][C:38]1[CH:39]=[C:40]([N:44]2[CH2:49][CH2:48][CH:47]([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)[CH2:46][CH2:45]2)[CH:41]=[CH:42][CH:43]=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 167528621-(3-Chlorophenyl)piperidin-4-oneHCID 220002791-(6-Methoxypyridin-3-yl)piperidin-4-one

Product 1

HCID 57814052N-[2-({(3R)-1-(1-(3-chlorophenyl)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-(3-chlorophenyl)piperidin-4-one was substituted for 1-(6-methoxypyridin-3-yl)piperidin-4-one, and was isolated as a white solid. 1H-NMR (CDCl3) δ: 1.87-2.10 (m, 5H), 2.37-2.44 (m, 1H), 2.66-2.74 (m, 2H), 2.86-2.95 (m, 2H), 3.03-3.09 (m, 1H), 3.55 (d, J=11.7 Hz, 1H), 3.64-3.76 (m, 3H), 4.06-4.23 (m, 2M), 4.79-4.83 (m, 1H), 6.74-6.78 (m, 1H), 6.83-6.85 (m, 2H), 7.13-7.18 (m, 1H), 7.53-7.57 (m, 1H), 7.66-7.75 (m, 2H), 8.09 (m, J=7.5 Hz, 1H), 8.20 (s, 1H), 8.28 (s, 1H), 9.09 (d, J=7.8 Hz, 1H). MS m/z: 509 (M+1).

Workup

  1. customwas isolated as a white solid

Sources & evidence

ORD record
ord-2e46da1e2b6c46fc89389b2a9da43494
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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