Rel-n-{2-[((3r,4r)-1-{1-[4-(morpholin-4-ylcarbonyl)phenyl]piperidin-4-yl}-4-propoxypyrrolidin-3-yl)amino]-2-oxoethyl}-3-(trifluoromethyl)benzamide → Rel-n-[2-({(3r,4r)-1-[1-(3-methylphenyl)piperidin-4-yl]-4-propoxypyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide

HRID 564409Notes

Reaction equation

HRID 564409 reaction equation
N1(C([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][CH:18]([N:21]4[CH2:25][C@@H:24]([O:26][CH2:27][CH2:28][CH3:29])[C@H:23]([NH:30][C:31](=[O:46])[CH2:32][NH:33][C:34](=[O:45])[C:35]5[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([F:44])([F:43])[F:42])[CH:36]=5)[CH2:22]4)[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=O)CCOCC1.N1(C(C2C=CC(N3CCC(=O)CC3)=CC=2)=O)CCOC[CH2:48]1>>[CH3:48][C:10]1[CH:11]=[C:12]([N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[CH2:25][C@@H:24]([O:26][CH2:27][CH2:28][CH3:29])[C@H:23]([NH:30][C:31](=[O:46])[CH2:32][NH:33][C:34](=[O:45])[C:35]4[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([F:43])([F:44])[F:42])[CH:36]=4)[CH2:22]3)[CH2:17][CH2:16]2)[CH:13]=[CH:14][CH:9]=1

Participants

3

Reactant 2

HCID 67004650Rel-n-{2-[((3r,4r)-1-{1-[4-(morpholin-4-ylcarbonyl)phenyl]piperidin-4-yl}-4-propoxypyrrolidin-3-yl)amino]-2-oxoethyl}-3-(trifluoromethyl)benzamideHCID 670046941-[4-(Morpholin-4-ylcarbonyl)phenyl]piperidin-4-one

Product 1

HCID 57814093Rel-n-[2-({(3r,4r)-1-[1-(3-methylphenyl)piperidin-4-yl]-4-propoxypyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide

Procedure

The title compound was synthesized in similar fashion to rel-N-{2-[((3R,4R)-1-{1-[4-(morpholin-4-ylcarbonyl)phenyl]piperidin-4-yl}-4-propoxypyrrolidin-3-yl)amino]-2-oxoethyl}-3-(trifluoromethyl)benzamide substituting 1-(3-methylphenyl)piperidin-4-one for 1-[4-(morpholin-4-ylcarbonyl)phenyl]piperidin-4-one and was isolated as a white solid. 1H-NMR (CDCl3) δ: 0.84 (m, J=7.6 Hz, 3H), 1.42-1.70 (m, 3H), 1.87-1.96 (m, 3H), 2.23 (s, 3H), 2.30-2.35 (m, 2H), 2.62-2.82 (m, 4H), 3.29-3.41 (m, 2H), 3.50-3.60 (m, 3H), 3.70-3.74 (m, 1H), 4.07 (d, J=4.8 Hz, 2H), 4.26-4.30 (m, 1H), 6.58-6.67 (m, 4H), 7.04-7.09 (m, 2H), 7.49 (t, J=7.9 Hz, 1H), 7.69 (d, J=7.8 Hz, 1H), 7.95 (d, J=7.5 Hz, 1H), 8.04 (s, 1H). MS m/z: 547 (M+1).

Workup

  1. customwas isolated as a white solid

Sources & evidence

ORD record
ord-0b73ed15c1c744b69291bedb65f2a29e
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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