1-(1,3-Benzodioxol-5-yl)piperidin-4-one → N-[2-({(3R)-1-[1-(1,3-benzodioxol-5-yl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide

HRID 564375Notes

Reaction equation

HRID 564375 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.[O:37]1C2C=CC(N3CCC(=O)CC3)=CC=2O[CH2:38]1.COC1N=CC(N2CCC(=O)CC2)=CC=1>>[O:2]1[C:3]2[CH:4]=[CH:5][C:6]([N:9]3[CH2:14][CH2:13][CH:12]([N:15]4[CH2:19][CH2:18][C@@H:17]([NH:20][C:21](=[O:36])[CH2:22][NH:23][C:24](=[O:35])[C:25]5[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:33])([F:34])[F:32])[CH:26]=5)[CH2:16]4)[CH2:11][CH2:10]3)=[CH:7][C:38]=2[O:37][CH2:1]1

Participants

4

Reactant 3

HCID 27285211-(1,3-Benzodioxol-5-yl)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 57813936N-[2-({(3R)-1-[1-(1,3-benzodioxol-5-yl)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-(1,3-benzodioxol-5-yl)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: 1.79-1.85 (m, 2H), 2.03-2.18 (m, 3H), 2.40-2.47 (m, 1H), 2.67 (t, J=11.4 Hz, 2H), 3.13-3.21 (m, 1H), 3.35-3.43 (m, 2H), 3.54-3.64 (m, 4H), 4.03 (s, 2H), 4.48-4.50 (m, 1H), 5.86 (s, 2H) 6.42 (dd, J=8.4, 2.4 Hz, 1H), 6.62 (d, J=2.4 Hz, 1H), 6.69 (m, J=8.4 Hz, 2H), 7.70 (t, J=7.9 Hz, 2H), 7.87 (d, J=7.5 Hz, 1H), 8.15 (d, J=8.1 Hz, 1H), 8.21 (s, 1H), 8.33 (s, 2H). MS m/z: 519 (M+1)

Workup

  1. customwas isolated as a white solid

Sources & evidence

ORD record
ord-528f5abdb3ae4b1dba4c64cddf22e56f
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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