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

HRID 564414Notes

Reaction equation

HRID 564414 reaction equation
[CH2:1]([O:4][C@@H:5]1[CH2:9][N:8]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[O:23])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH2:7][C@H:6]1[NH:30][C:31](=[O:46])[CH2:32][NH:33][C:34](=[O:45])[C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([F:44])([F:43])[F:42])[CH:36]=1)[CH:2]=[CH2:3]>CO.[Pd]>[N:24]1([C:22]([C:19]2[CH:20]=[CH:21][C:16]([N:13]3[CH2:12][CH2:11][CH:10]([N:8]4[CH2:9][C@@H:5]([O:4][CH2:1][CH2:2][CH3:3])[C@H:6]([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:42])([F:43])[F:44])[CH:36]=5)[CH2:7]4)[CH2:15][CH2:14]3)=[CH:17][CH:18]=2)=[O:23])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1

Participants

4

Reactant 1

HCID 67004679Rel-n-{2-[((3r,4r)-4-(allyloxy)-1-{1-[4-(morpholin-4-ylcarbonyl)phenyl]piperidin-4-yl}pyrrolidin-3-yl)amino]-2-oxoethyl}-3-(trifluoromethyl)benzamide

Product 1

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)benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of rel-N-{2-[((3R,4R)-4-(allyloxy)-1-{1-[4-(morpholin-4-ylcarbonyl)phenyl]piperidin-4-yl}pyrrolidin-3-yl)amino]-2-oxoethyl}-3-(trifluoromethyl)benzamide in methanol (400 μL) was added and palladium (10%) on carbon (50 mg) was added and purged with hydrogen gas for two minutes; the reaction was then subjected to 1 atmosphere of hydrogen gas overnight. The flask was purged with argon; the mixture was filtered, then purified by preparative HPLC to afford the title compound as a white solid. 1H-NMR (CDCl3) δ: 0.82 (t, J=7.8 Hz, 3H), 1.43-1.53 (m, 2H), 1.59-1.68 (m, 1H), 1.89-1.93 (m, 2H), 2.46-2.51 (m, 2H), 2.73 (t, J=11.4 Hz, 2H), 2.85-2.96 (m, 2H), 3.10-3.20 (m, 2H), 3.29-3.36 (m, 2H), 3.41-3.69 (m, 10H), 3.79 (b, 1H), 4.05 (d, J=4.5 Hz 2H), 4.29-4.33 (%, 1 μl), 6.79 (d, J=8.7 Hz, 2H), 7.25 (d, J=9.0 Hz, 2H), 7.43-7.49 (m, 1H), 7.67 (d, J=8.4 Hz, 1H), 7.97 (d, J=7.5 Hz, 1H), 8.07 (s, 1H). MS m/z: 646 (M+1).

Workup

  1. custompurged with hydrogen gas for two minutes
  2. customwas then subjected to 1 atmosphere of hydrogen gas overnight
  3. customThe flask was purged with argon
  4. filtrationthe mixture was filtered
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-0bb6a8ee38db48d3b07f736387f88a07
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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