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

HRID 564382Notes

Reaction equation

HRID 564382 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.[CH3:37][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>>[CH3:37][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 213505521-(3-Methylphenyl)Piperidin-4-OneHCID 220002791-(6-Methoxypyridin-3-yl)piperidin-4-one

Product 1

HCID 57814127N-[2-({(3R)-1-[1-(3-methylphenyl)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-methylphenyl)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: 1.77-1.87 (m, 2H), 2.04-2.19 (m, 3H), 2.40-2.47 (m, 1H), 2.74 (t, J=12.7 Hz, 2H), 3.16-3.24 (m, 1H), 3.34-3.42 (r, 2H), 3.54-3.63 (m, 2H), 3.77 (t, J=12.9 Hz, 2H), 4.03 (s, 2H), 4.48-4.52 (m, 1H), 6.68 (d, J=7.5 Hz, 1H), 6.75-6.80 (m, 2H), 7.10 (t, J=7.9 Hz, 1H), 7.11 (t, J=7.9 Hz, 1H), 7.69 (t, J=7.9 Hz, 2H), 7.87 (d, J=8.1 Hz, 1H), 8.15 (d, J=7.8 Hz, 1H), 8.22 (s, 1H), 8.36 (s, 1H). MS m/z: 489 (M+1).

Workup

  1. customwas isolated as a white solid

Sources & evidence

ORD record
ord-69d4f572b3b543768b312ef78fb7fd4d
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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